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Chemistry
Heterocyclic Building Blocks
Naphthyridines
3-Bromo-8-chloro-1,7-naphthyridine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Naphthyridines
Bromides Chlorides

[ CAS No. 1260670-05-0 ] {[proInfo.proName]}

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Product Details of [ 1260670-05-0 ]

CAS No. :1260670-05-0 MDL No. :MFCD18250850
Formula : C8H4BrClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :DSPVDMUXVYEYPP-UHFFFAOYSA-N
M.W : 243.49 Pubchem ID :72213592
Synonyms :

Safety of [ 1260670-05-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1260670-05-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1260670-05-0 ]

[ 1260670-05-0 ] Synthesis Path-Downstream   1~53

  • 1
  • [ 794592-13-5 ]
  • [ 1260670-05-0 ]
Reference： [1]Patent: WO2013/54291,2013,A1
  • 2
  • [ 1400645-41-1 ]
  • [ 1260670-05-0 ]
Reference： [1]Patent: WO2013/54291,2013,A1
[2]Patent: CN111039942,2020,A
  • 3
  • [ 1429870-16-5 ]
  • [ 1260670-05-0 ]
Reference： [1]Patent: WO2013/54291,2013,A1
  • 4
  • [ 1375301-90-8 ]
  • [ 1260670-05-0 ]
YieldReaction ConditionsOperation in experiment
1.1 g With N-ethyl-N,N-diisopropylamine; trichlorophosphate; In toluene; at 130.0℃; for 36.0h; 3-Bromo-7H-[1 ,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCI3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130 C for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1 .1 g, 4.52 mmol).HPLC: RtH9= 0.86 min; ESIMS [M+H]+ = 242.8, 244.8, 246.8 (1 Br,1 CI);1H-NMR (400 MHz, DMSO-d6): delta 9.22 (d, 1 H), 8.95 (2, 1 H), 8.49 (d, 1 H), 7.99 (d, 1 H).
Reference： [1]Patent: WO2013/54291,2013,A1 .Location in patent: Page/Page column 77-78
  • 5
  • [ 1262859-09-5 ]
  • [ 1260670-05-0 ]
  • [ 1429869-84-0 ]
Reference： [1]Patent: WO2013/54291,2013,A1
  • 6
  • [ 1262859-09-5 ]
  • [ 1260670-05-0 ]
  • [ 1429869-83-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In 1,4-dioxane; tert-butyl alcohol; at 100℃; for 1.0h;Microwave irradiation; [(R)-5-(5-Amino-2-fluoro-phenyl)-5-difluoromethyl-5,6-dihydro-2H-[1 ,4] oxazin-3-yl]-carbamic acid tert-butyl ester (CAS registry 1262859-09-5) (250 mg, 0.696 mmol) and 3-bromo-8- chloro-[1 ,7]naphthyridine [Heteroaryl 1] (186 mg, 0.765 mmol) were dissolved in tert-Butanol (4 ml) in a microwave vial and HCI (0.174 ml of a 4M solution in dioxane) was added. The vial was sealed and heated to 100 C for 1 h. The reaction mixture was cooled to rt and added to a saturated NaHC03 solution (20 ml) and stirred at rt for 10 min.The solution was extracted with DCM (2 x 30 ml). The combined organic layer was washed with NaHC03 solution and brine, treated with MgS04, filtered and to give the desired product. HPLC: RtH9= 0.90 min; ESIMS [M+H]+ = 465.9/467.9(1 Br);1H-NMR (400 MHz, CDCI3): delta 8.90 (s, 1 H), 8.64 (m, 1 H), 8.27 (m, 1 H), 8.08 (d, 1 H), 7.90 (dd, 1 H), 7.10 (dd, 1 H), 6.82 (d, 1 H), 6.34-6.06 (t, 1 H), 4.35 (dd, 1 H), 4.18 (d, 1 H), 4.07 (d, 1 H), 3.96 (d, 1 H).19F-NMR (376 MHz, CDCI3): delta - 1 19.6 (s), (- 126.53) - (- 129.20) (dq).
Reference： [1]Patent: WO2013/54291,2013,A1 .Location in patent: Page/Page column 63
  • 7
  • [ 1260670-05-0 ]
  • tert-butyl (R)-(4-(5-amino-2-fluorophenyl)-2,4,7,7-tetramethyl-1,1-dioxido-1,2,5-thiadiazepan-6-ylidene)carbamate [ No CAS ]
  • (R)-tert-butyl (4-(5-((3-bromo-1,7-naphthyridin-8-yl)amino)-2-fluorophenyl)-2,4,7,7-tetramethyl-1,1-dioxido-1,2,5-thiadiazepan-6-ylidene)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hexamethylsilazane; In tetrahydrofuran; N,N-dimethyl acetamide; at 50℃; for 2.0h; Step 2 - Synthesis of tert-butyl (R)-(4-(5-((3-bromo-l, 7-naphthyridin-8-yl)amino)-2- fluorophenyl)-2,4, 7, 7-tetramethyl-l, l-dioxido-l,2,5-thiadiazepan-6-ylidene)carbamate To a solution of 3-bromo-8-chloro-l,7-naphthyridine (205 mg, 0.840 mmol) and (R)-tert- butyl (4-(5-amino-2-fluorophenyl)-2,4,7,7-tetramethyl- 1 , 1 -dioxido- 1 ,2,5-thiadiazepan-6- ylidene) carbamate (300 mg, 0.70 mmol) in DMA (3 mL) was added KHMDS (2.45 mL, 2.45 mmol, 1.0 M in THF). The mixture was heated to 50 C and stirred for 2 h. The mixture was cooled and diluted with ethyl acetate. After separation, the organic layer was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with 0-5% MeOH in DCM, to afford the desired product.
Reference： [1]Patent: WO2015/95104,2015,A1 .Location in patent: Page/Page column 76
  • 8
  • [ 764-01-2 ]
  • [ 1260670-05-0 ]
  • [ 1620981-39-6 ]
YieldReaction ConditionsOperation in experiment
With 5-(di-tert-butylphosphino)-1?, 3?, 5?-triphenyl-1?H-[1,4?]bipyrazole; palladium diacetate; caesium carbonate; at 70℃; for 4.0h;Inert atmosphere; Step 1 To a mixture of 3-bromo-8-chloro-l ,7-naphthyridine J-1 (4.00 g, 16.4 mmol), but-2-yn-l-ol (1.78 g, 24.6 mmol), Cs2C03 (8.03 g, 24.6 mmol), and 5-(di-ieri-butylphosphino)-l',3',5'- triphenyl-rH-l ,4'-bipyrazole (1.67 g, 3.29 mmol) in THF (40 mL) was added diacetoxypalladium (0.574 g, 1.64 mmol) under N2. The mixture was stirred at 70 C for 4 h and concentrated; the residue was purified directly by silica column chromatography (PE: EtOAc = 3: 1) to afford compound J-2. MS for J-2: m/e = 233 (M+l).
Reference： [1]Patent: WO2015/187437,2015,A1 .Location in patent: Page/Page column 67; 68
  • 9
  • [ 1260670-05-0 ]
  • 8-bromo-3-(but-2-yn-1-yloxy)-1,7-naphthyridine [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 10
  • [ 1260670-05-0 ]
  • 3-bromo-1,7-naphthyridin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With ammonium hydroxide; In tetrahydrofuran; at 100℃;Sealed tube; Ammonium hydroxide (40 mL, 1.04 mol, 28%) was added to a solution of 3-bromo- 8-chloro-l,7-naphthyridine (1.00 g, 4.11 mmol) and THF (10 mL) in a sealed tube. The mixture was sealed, stirred at 100 C overnight, diluted with H20 (100 mL), and then extracted with EtOAc (3 x50 mL). The combined organic layers were washed (2x 100 mL brine), dried (Na2S04), filtered, and concentrated to dryness to give Intermediate 9 (824 mg, 89%) as a yellow solid. 1H NMR (400MHz, DMSO-i): delta 8.81 (s, 1H), 8.51 (s, 1H), 7.90 (d, 1H), 7.05 (br s, 2H), 6.87 (d, 1H); MS: 223.9 [M+H]+.
With ammonium hydroxide; In 1,4-dioxane; at 100℃; for 15.0h;Sealed tube; Step 1 To a 100 mL sealed tube was added 3~bromo-8-chloro-l,7-naphthyridine K-l (1.00 g, 4.10 mmol), 1,4-dioxane (15 mL) and NH3_H20 (40 mL) at room temperature. The mixture was sealed and stirred at 100 C for 15 h, then cooled and partitioned between water (150 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (50 mL x 2) and the combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to afford compound K-2. MS for K-2: m/e = 224 and 226 (M+l).
Reference： [1]Patent: WO2018/170167,2018,A1 .Location in patent: Paragraph 00350
[2]Patent: WO2015/187437,2015,A1 .Location in patent: Page/Page column 68
  • 11
  • [ 1260670-05-0 ]
  • C18H22BrN3O4 [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 12
  • [ 1260670-05-0 ]
  • C9H6N4 [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 13
  • [ 1260670-05-0 ]
  • C22H21FN8O2S*C2HF3O2 [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 14
  • [ 1260670-05-0 ]
  • C26H27FN6O3S*C2HF3O2 [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 15
  • [ 1260670-05-0 ]
  • C31H34F2N6O5S [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 16
  • [ 1260670-05-0 ]
  • C26H26F2N6O3S*C2HF3O2 [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 17
  • [ 1260670-05-0 ]
  • C19H26F2N4O4S [ No CAS ]
  • C22H21BrF2N6O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 2 To a stirred solution of intermediate M-2 (90.0 mg, 0.20 mmol) and 3-bromo-8-chloro-l ,7- naphthyridine (74.0 mg, 0.30 mmol) in THF (3 mL) was added LHMDS (1 M in THF, 0.510 mL, 0.51 mmol) at RT and the mixture was heated at 45 C. After 2 h, additional 1 eq. of LHMDS was added and the mixture was stirred overnight at 45 C. The reaction was quenched with saturated NH4C1 and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The resulting residue was treated with 5 mL of DCM and TFA (0.5 mL) was added. The mixture was stirred at 25 C for 2 h, then nuetralized with saturated NaHC03 and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by p-TLC (DCM: MeOH = 15 : 1) to afford compound M-3. MS for M-3: m/e = 551 and 553 (M+l).
Reference： [1]Patent: WO2015/187437,2015,A1 .Location in patent: Page/Page column 72; 73
  • 18
  • [ 1260670-05-0 ]
  • C19H26F2N4O4S [ No CAS ]
  • C23H21F2N7O2S*C2HF3O2 [ No CAS ]
Reference： [1]Patent: WO2015/187437,2015,A1
  • 19
  • [ 1260670-05-0 ]
  • C20H28FN3O4S [ No CAS ]
  • 3-bromo-N-{3-[(3R,6S)-6-cyclopropyl-5-imino-3,6-dimethyl-1,1-dioxidothiomorpholin-3-yl]-4-fluorophenyl}-1,7-naphthyridin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium hexamethyldisilazane; In tetrahydrofuran; at 45℃; for 14.0h; Step 1 To a stirred solution of intermediate A-10 (1.43 g, 3.36 mmol) and 3-bromo-8-chloro-l,7- naphthyridine (0.982 g, 4.03 mmol) in THF (34 ml) was added LHMDS in THF (11.8 ml, 11.8 mmol) at RT. The mixture was stirred at 45 C for 14 h, cooled, and diluted with dichloromethane (200 mL) and water (50 ml). The organic layers were collected, dried with magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography (120 g of Si02> 0-100% EtOAc in hexane) to provide example 17. MS for example 17: m/e = 532 and 534 (M+l).
Reference： [1]Patent: WO2015/187437,2015,A1 .Location in patent: Page/Page column 82
  • 20
  • [ 1260670-05-0 ]
  • tert-butyl ((2S,5R)-5-(2-amino-5-fluoropyridin-4-yl)-2-cyclopropyl-2,5-dimethyl-1,1-dioxidothiomorpholin-3-ylidene)carbamate [ No CAS ]
  • 3-bromo-N-{4-[(3R,6S)-6-cyclopropyl-5-imino-3,6-dimethyl-1,1-dioxidothiomorpholin-3-yl]-5-fluoropyridin-2-yl}-1,7-naphthyridin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Method N B-9 Ex. 3 To a stirred solution of Intermediate B-9 (400 mg, 0.937 mmol) and 3-bromo-8-chloro-l,7- naphthyridine (252 mg, 1.03 mmol) in THF (10 mL) was added LHMDS (1 M in THF, 3.28 mL, 3.28 mmol) at RT. The mixture was stirred at 45 C overnight, quenched with NH CI (sat.) and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The residue was treated with 5 mL of DCM and 0.5 mL of TFA and stirred at 25 C for 2 h. The mixture was neutralized with NaHC03 and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by silica column chromatography (PE: EtOAc = 1 : 1) to afford example 3. MS for example 3: m/e = 533 and 535 (M+l).
Reference： [1]Patent: WO2015/187437,2015,A1 .Location in patent: Page/Page column 73
  • 21
  • [ 1260670-05-0 ]
  • tert-butyl ((2S,5R)-5-(5-amino-2-fluorophenyl)-2-cyclopropyl-2-(fluoromethyl)-5-methyl-1,1-dioxidothiomorpholin-3-ylidene)carbamate [ No CAS ]
  • C23H22BrF2N5O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 1 To a stirred solution of intermediate D-7 (200 mg, 0.45 mmol) and 3-bromo-8-chloro-l ,7- naphthyridine (165 mg, 0.68 mmol) in THF (8 mL) was added LHMDS (1 M in THF, 1.13 mL, 1.13 mmol) at RT. The mixture was stirred at 45 C for 2 h, then an additional 1 eq. of LHMDS was added and the mixture was stirred at 45 C overnight. The mixture was diluted with saturated Nu0 and extracted with DCM. The combined organic extracts were dried over Na2S04 and concentrated. The resulting residue was rediluted with 5 mL of DCM and TFA (0.5 mL) was added. The resulting mixture was stirred at 25 C for 2 h, then neutralized with NaHC03, and extracted with DCM. The organic layer was washed with brine, dried over Na2S04 and concentrated. The residue was purified by prep-TLC (DCM: MeOH = 15 : 1) to afford compound L-1. MS for L-1 : m/e = 550 and 552 (M+l).
Reference： [1]Patent: WO2015/187437,2015,A1 .Location in patent: Page/Page column 71
  • 22
  • [ 1260670-05-0 ]
  • C23H37FN4O5S [ No CAS ]
  • (1S,5R)-5-(5-((3-bromo-1,7-naphthyridin-8-yl)amino)-2-fluorophenyl)-3-imino-2,2,5-trimethyl-1-(methylimino)-1λ6-thiomorpholine 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Parallel preparation of examples 6-7: To a set of vials containing the requisite aryl halide (0.20 mmol) was added a solution of HI (50 mg, 0.10 mmol) in THF (1.0 mL). The vials were capped and transferred into a glove box under an atmosphere of nitrogen. To each vial was then added a solution of LHMDS (1.0 M in THF, 0.25 mL, 0.25 mmol). The mixtures were then heated at 50 C with stirring overnight. After that time, water (2 mL) and DCM (2 mL) were added to each vial. The mixtures were transferred to a set of fritted barrel filters. The organic layer from each vial was drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. To each vial was then added water (0.050 mL) and TFA (0.5 mL). The mixtures were stirred at 50C with stirring overnight. After that time, the mixtures were concentrated in vacuo. The crude residues were dissolved in DMSO (1 mL) and filtered. The crude residue containing Example 6 was purified by mass triggered preparative HPLC. [column: Waters XBridge CI 8, 5mupiiota , 19x100 mm; solvent: gradient 35-70% MeCN (0.1% NH4OH) in water (0.1% NH4OH) 25 mL/min; 8 min run time] to afford Example 6. The crude residue containing Example 7 was purified by mass triggered preparative HPLC [Waters Sunfire CI 8 column, 5muetaiota, 19 100 mm, using a gradient from 10% initial to 45% final MeCN (0.1% TFA) in water (0.1% TFA), 25 mL/min, 8 min run time] to afford Example 7.
Reference： [1]Patent: WO2016/40226,2016,A1 .Location in patent: Page/Page column 52-53
  • 23
  • [ 1260670-05-0 ]
  • (R)-tert-butyl (5-(5-amino-2-fluorophenyl)-2,5-dimethyl-1,1-dioxido-1,2,4-thiadiazinan-3-ylidene)carbamate [ No CAS ]
  • C24H26BrFN6O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium hexamethyldisilazane; In tetrahydrofuran; at 25 - 45℃; for 4.0h; Step 1To a stirred solution of (R)-tert-butyl (5-(5-amino-2-fluorophenyl)-2,5 -dimethyl -1,1- dioxido-l,2,4-thiadiazinan-3-ylidene)carbamate A9 (250 mg, 0.647 mmol) and 3-bromo-8- chloro-l,7-naphthyridine (205 mg, 0.841 mmol) in THF (6.47 ml) was added LiHMDS (1M in THF, 1.617 ml, 1.617 mmol) at room temperature. The mixture was stirred at 45 C for 4h. It was diluted with saturated ammonium chloride and extracted with DCM (3x). The organics were combined, dried over magnesium sulfate, filtered and concentrated. The residue was redissolved in DCM (3 mL) and TFA (0.249 ml, 3.23 mmol) added and the reaction stirred for 15h. The reaction was quenched with saturated sodium bicarbonate and extracted with DCM (3x). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography EtOAc in DCM to afford example 2. MS for example 2: m/e = 493 (M+l).
Reference： [1]Patent: WO2016/118404,2016,A1 .Location in patent: Page/Page column 41
  • 24
  • [ 1260670-05-0 ]
  • [ 100-53-8 ]
  • 3-(benzylthio)-8-chloro-1,7-naphthyridine [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1062 - 1067
  • 25
  • [ 1260670-05-0 ]
  • perfluorophenyl 8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine-3-sulfonate [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1062 - 1067
  • 26
  • [ 1260670-05-0 ]
  • C27H21F3N4O4S2 [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1062 - 1067
  • 27
  • [ 1260670-05-0 ]
  • 8-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)-1,7-naphthyridine-3-sulfonamide [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1062 - 1067
  • 28
  • [ 1260670-05-0 ]
  • C16H10ClF3N2O3S [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1062 - 1067
  • 29
  • [ 1260670-05-0 ]
  • 3-(benzylthio)-8-(2-methoxy-4-(trifluoromethyl)phenyl)-1,7-naphthyridine [ No CAS ]
Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1062 - 1067
  • 30
  • [ 1260670-05-0 ]
  • [ 172975-98-3 ]
  • [ 75-65-0 ]
  • 3-bromo-N-(2-methylbiphenyl-3-yl)-1, 7-naphthyridin-8-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; Step 1: 3-bromo-N-(2-methylbiphenyl-3-yl)-1, 7-naphthyridin-8-amine To a microwave vial was added 2-methylbiphenyl-3-amine (Example 1, Step 1: 0.1 g, 0.546 mmol), <strong>[1260670-05-0]3-bromo-8-chloro-1,7-naphthyridine</strong> (PharmaBlock, cat#PBLJ2743: 140 mg, 0.55 mmol), tert-butyl alcohol (2.5 mL) and 4.0 M hydrogen chloride in dioxane (0.136 mL, 0.546 mmol). The resulting mixture was irradiated in the microwave to 100 C. for 1 h. The resulting mixture was concentrated, and the desired product was used directly in the next step. LC-MS calculated for C21H17N3Br (M+H)+: m/z=390.1; found 390.1.
Reference： [1]Patent: US2017/174679,2017,A1
  • 31
  • [ 1260670-05-0 ]
  • C18H25FN4O4S [ No CAS ]
  • (4aR,7aR)-4a-(5-((3-bromo-1,7-naphthyridin-8-yl)amino)-2-fluorophenyl)-3-imino-2-methyloctahydrocyclopenta[e][1,2,4]thiadiazine 1,1-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: To a set of vials containing the requisite aryl halide(0.15 mmol) was added a solution of Bi (30 mg, 0.073 mmol) in THF (1.0 mL). The vials werecapped and transferred into a glove box under an atmosphere of nitrogen. To each vial was then added a solution of LHMDS (1.0 M in THF). The mixtures were then heated at 50 C with stirring overnight. After that time, water (2 mL) and DCM (2 mL) were added to each vial. The mixtures were transferred to a set of fritted barrel filters. The organic layer from each vialwas drained into a clean vial. Additional DCM (1 mL) was added to each aqueous layer and the organic layer was again drained and combined with the previous organic extract. The solvent from the combined organic layers was removed in vacuo. To each vial was then added DCM (1 mL) and TFA (0.5 mL). The mixtures were stirred at RT for 2 hours. After that time, the mixtures were concentrated in vacuo. The crude residues were dissolved in DMSO (1 mL) andfiltered. The crude products were purified by mass triggered preparative HPLC [Waters Sunfire C18 column, Sum, 19x100 mm, using a gradient from 10% initial to 40% final MeCN (0.1% TFA) in water (0.1% TFA), 25 mL/min, 8 mm run timej to afford Examples 22-23.
Reference： [1]Patent: WO2017/95759,2017,A1 .Location in patent: Page/Page column 60; 61
  • 32
  • [ 1260670-05-0 ]
  • [ 75927-49-0 ]
  • 8-chloro-3-vinyl-1,7-naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In ethanol; water; toluene; at 100℃; for 16.0h;Inert atmosphere; To a solution of <strong>[1260670-05-0]3-bromo-8-chloro-1,7-naphthyridine</strong> (2.43g) in toluene (30 mL), EtOH (10 mL), and 10%Na 2CO 3 aq. (10 mL)pd (dppf) Cl 2. DCM (420 mg) was added. 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (3.1g) was added dropwise under N 2 protection. The mixture was allowed to stir at 100C for 16h. The reaction was quenched by H 2O (50 mL)and extracted by EtOAc for 3 times. Organic layer was combined and washed with brine. The resulting solution was concentrated and purified by silicagel (eluting with hexane-EtOAc using a gradient from 8: 1 to 5: 1) to afford 8-chloro-3-vinyl-1,7-naphthyridine (1.1g)as a brown solid. 88%).
76.1% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 1.5h;Inert atmosphere; Reflux; Starting compound 5 (9.6g, 39.4mmol, 1eq),Vinylboronic acid pinacol ester (6.68g, 43.4mmol, 1.1eq),Sodium carbonate (20.9g, 197.1mmol, 5eq) was added to the THF-water (4: 1,480mL, 50V) mixed solvent,After nitrogen substitution, tetratriphenylphosphine palladium (911.2mg, 0.79mmol, 0.02eq) was added,After nitrogen replacement again, stirring and heating to reflux,After 1.5h, TLC and LCMS analyzed a small amount of raw materials remaining.After the heat was turned off, after the system was concentrated, the residue was extracted three times with EA, and the organic phases were combined,It was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and column chromatography (EA in Hep 15%),The product compound 6 was obtained as a light yellow solid 5.9 g, and the yield was 76.1%.
With [1,1?-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II); sodium carbonate; In water; tert-butyl alcohol; at 110℃; for 2.0h;Inert atmosphere; Sealed tube; A mixture of <strong>[1260670-05-0]3-bromo-8-chloro-1,7-naphthyridine</strong> (PharmaBlock catPBLJ2743: 0.200 g, 0.821 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (Aldrich cat663348: 153 muL, 0.904 mmol), sodium carbonate (0.174 g, 1.64 mmol) and [1,1?-bis(dicyclohexylphosphino)ferrocene]dichloropalladium( II) (Aldrich cat701998: 6.2 mg, 0.0082 mmol) in tert-butyl alcohol (5.91 mL, 61.8 mmol) and water (6 mL, 300 mmol) was degassed and sealed. It was stirred at 110 C. for 2 h. The reaction mixture was cooled to room temperature then extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was used directly in the next step without further purification. LC-MS calculated for C10H8ClN2 (M+H)+: m/z=191.0; found 191.0.
1.1 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In ethanol; water; toluene; at 100℃; for 16.0h;Inert atmosphere; To a solution of 3-bromo-8-chloro-1, 7-naphthyridine (2.43g) in toluene (30mL) , EtOH (10mL) , and 10%Na2CO3aq. (10mL) Pd (dppf) Cl2.DCM (420mg) was added. 4, 4, 5, 5-tetramethyl-2-vinyl-1, 3, 2-dioxaborolane (3.1g) was added dropwise under N2protection. The mixture was allowed to stir at 100 for 16 h. The reaction was quenched by H2O (50mL) and extracted by EtOAc for 3 times. Organic layer was combined and washed with brine. The resulting solution was concentrated and purified by silicagel (eluting with hexane-EtOAc using a gradient from 8: 1 to 5: 1) to afford 8-chloro-3-vinyl-1, 7-naphthyridine (1.1g) as a brown solid.

Reference： [1]Patent: WO2020/15716,2020,A1 .Location in patent: Page/Page column 18; 19
[2]Patent: CN111039942,2020,A .Location in patent: Paragraph 0439; 0464-0468
[3]Patent: US2018/177784,2018,A1 .Location in patent: Paragraph 0639-0640
[4]Patent: WO2019/192506,2019,A1 .Location in patent: Page/Page column 60
[5]Patent: WO2020/11243,2020,A1 .Location in patent: Page/Page column 21
  • 33
  • [ 1260670-05-0 ]
  • 2-[(3-[(2-hydroxyethyl)amino]methyl}-1,7-naphthyridin-8-yl)amino]-4-phenylthiophene-3-carbonitrile trifluoroacetate [ No CAS ]
Reference： [1]Patent: US2018/177784,2018,A1
  • 34
  • [ 1260670-05-0 ]
  • 8-chloro-1, 7-naphthyridine-3-carbaldehyde [ No CAS ]
Reference： [1]Patent: US2018/177784,2018,A1
[2]Patent: WO2019/192506,2019,A1
[3]Patent: WO2020/11243,2020,A1
[4]Patent: WO2020/15716,2020,A1
[5]Patent: CN111039942,2020,A
  • 35
  • [ 1260670-05-0 ]
  • 2-[(8-chloro-1, 7-naphthyridin-3-yl)methyl]amino}ethanol [ No CAS ]
Reference： [1]Patent: US2018/177784,2018,A1
  • 36
  • [ 1260670-05-0 ]
  • (8-chloro-1,7-naphthyridin-3-yl)methanol [ No CAS ]
Reference： [1]Patent: WO2019/192506,2019,A1
[2]Patent: WO2020/11243,2020,A1
[3]Patent: WO2020/15716,2020,A1
  • 37
  • [ 1260670-05-0 ]
  • (8-((3-bromo-2-methylphenyl)amino)-1,7-naphthyridin-3-yl)methanol [ No CAS ]
Reference： [1]Patent: WO2019/192506,2019,A1
[2]Patent: WO2020/11243,2020,A1
[3]Patent: WO2020/15716,2020,A1
  • 38
  • [ 1260670-05-0 ]
  • (8-((2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)amino)-1,7-naphthyridin-3-yl)methanol [ No CAS ]
Reference： [1]Patent: WO2019/192506,2019,A1
[2]Patent: WO2020/11243,2020,A1
  • 39
  • [ 1260670-05-0 ]
  • (((2,2'-dimethyl-[1,1'-biphenyl]-3,3'-diyl)bis(azanediyl))bis(1,7-naphthyridine-8,3-diyl))dimethanol [ No CAS ]
Reference： [1]Patent: WO2019/192506,2019,A1
[2]Patent: WO2019/192506,2019,A1
  • 40
  • [ 1260670-05-0 ]
  • 2-((8-((3'-((3-(((2-hydroxyethyl)amino)methyl)-1,7-naphthyridin-8-yl)amino)-2,2'-dimethyl-[1,1'-biphenyl]-3-yl)amino)quinolin-3-yl)amino)ethan-1-ol [ No CAS ]
Reference： [1]Patent: WO2019/192506,2019,A1
  • 41
  • [ 1260670-05-0 ]
  • ((8-((2,2'-dimethyl-3'-(3-morpholinopropoxy)-[1,1'-biphenyl]-3-yl)amino)-1,7-naphthyridin-3-yl)methyl)glycine [ No CAS ]
Reference： [1]Patent: WO2020/15716,2020,A1
  • 42
  • [ 1260670-05-0 ]
  • methyl ((8-chloro-1,7-naphthyridin-3-yl)methyl)glycinate [ No CAS ]
Reference： [1]Patent: WO2020/15716,2020,A1
  • 43
  • [ 1260670-05-0 ]
  • methyl ((8-((3-bromo-2-methylphenyl)amino)-1,7-naphthyridin-3-yl)methyl)glycinate [ No CAS ]
Reference： [1]Patent: WO2020/15716,2020,A1
  • 44
  • [ 1260670-05-0 ]
  • methyl ((8-((2,2'-dimethyl-3'-(3-morpholinopropoxy)-[1,1'-biphenyl]-3-yl)amino)-1,7-naphthyridin-3-yl)methyl)glycinate [ No CAS ]
Reference： [1]Patent: WO2020/15716,2020,A1
  • 45
  • [ 1260670-05-0 ]
  • methyl ((8-((2-methyl-[1,1'-biphenyl]-3-yl)amino)-1,7-naphthyridin-3-yl)methyl)glycinate [ No CAS ]
Reference： [1]Patent: WO2020/15716,2020,A1
  • 46
  • [ 156072-86-5 ]
  • [ 1260670-05-0 ]
Reference： [1]Patent: CN111039942,2020,A
  • 47
  • [ 886365-43-1 ]
  • [ 1260670-05-0 ]
Reference： [1]Patent: CN111039942,2020,A
  • 48
  • C10H12BrN3O [ No CAS ]
  • [ 1260670-05-0 ]
Reference： [1]Patent: CN111039942,2020,A
  • 49
  • 3-bromo-1,7-naphthyridin-8-ol [ No CAS ]
  • [ 1260670-05-0 ]
YieldReaction ConditionsOperation in experiment
65.7% With trichlorophosphate; for 2.0h;Reflux; Compound 4 (13.5g, 60.0mmol, 1eq)Mixed with phosphorus oxychloride (135mL, 10V), stirred and heated to reflux for 2h, LCMS showed that the reaction was completed,Concentrate, dilute the residue with water, add EA to beat for 1h,After filtering, the filter cake was washed with water, and after drying, the product was obtained as a light yellow solid, 9.6 g, and the yield was 65.7%.
Reference： [1]Patent: CN111039942,2020,A .Location in patent: Paragraph 0439; 0459-0463
  • 50
  • [ 1260670-05-0 ]
  • C29H32ClN3OSi [ No CAS ]
Reference： [1]Patent: CN111039942,2020,A
  • 51
  • [ 1260670-05-0 ]
  • C45H48N4O3Si [ No CAS ]
Reference： [1]Patent: CN111039942,2020,A
  • 52
  • [ 1260670-05-0 ]
  • C44H46N4O3Si [ No CAS ]
Reference： [1]Patent: CN111039942,2020,A
  • 53
  • [ 1260670-05-0 ]
  • (1r,4r)‐4‐({2‐[(2,2'‐dimethyl‐3'‐{4‐oxo‐5H,6H,7H‐[1,3]thiazolo[4,5‐c]pyridin‐2‐yl}‐[1,1'‐biphenyl]‐3‐yl)carbamoyl]‐1‐methyl‐4H,6H,7H‐imidazo[4,5‐c]pyridin‐5‐yl}methyl)cyclohexane‐1‐carboxylic acid [ No CAS ]
Reference： [1]Patent: CN111039942,2020,A

Tags: 1260670-05-0 synthesis path| 1260670-05-0 SDS| 1260670-05-0 COA| 1260670-05-0 purity| 1260670-05-0 application| 1260670-05-0 NMR| 1260670-05-0 COA| 1260670-05-0 structure

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