Home Cart 0 Sign in  

[ CAS No. 660830-62-6 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 660830-62-6
Chemical Structure| 660830-62-6
Structure of 660830-62-6 *Storage: {[proInfo.prStorage]}

Quality Control of [ 660830-62-6 ]

Related Doc. of [ 660830-62-6 ]

SDS
Alternatived Products of [ 660830-62-6 ]
Alternatived Products of [ 660830-62-6 ]

Product Details of [ 660830-62-6 ]

CAS No. :660830-62-6MDL No. :MFCD13195308
Formula : C12H10BrNO2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :280.12Pubchem ID :69083434
Synonyms :

Computed Properties of [ 660830-62-6 ]

TPSA : 39.2 H-Bond Acceptor Count : 3
XLogP3 : 3.3 H-Bond Donor Count : 0
SP3 : 0.17 Rotatable Bond Count : 3

Safety of [ 660830-62-6 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 660830-62-6 ]

  • Upstream synthesis route of [ 660830-62-6 ]
  • Downstream synthetic route of [ 660830-62-6 ]

[ 660830-62-6 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 660830-62-6 ]
  • [ 660830-63-7 ]
YieldReaction ConditionsOperation in experiment
85% With lithium hydroxide; water In tetrahydrofuran; methanol at 0℃; for 0.5 h; To a solution of 4-bromophthalic acid (3.0 g, 12.24 [MMOL)] in 30 mL of THF was added a solution of borane-THF complex (1. OM) dropwise at 0 [°C.] The solution was warmed to rt and stirred for 3 h. The reaction mixture was quenched by addition of HCI (2N) at 0 [°C.] The product was extracted with ethyl acetate and washed with sat. [NACI,] dried over [NA2SC4,] and concentrated under reduced pressure to afford 2.8 g (100percent) of 4-bromo-2- hydroxymethylbenzyl alcohol as a [COLORLESS OIL.APOS;H] NMR [(CDCK)] 7.28 (m, 2 H), 7.26 (m, 1 H), 4.69 (s, 4 H), 2.80 (bs, [2 H).] To a solution of oxalyl chloride (2.37 mL, 4.607 mmol) in DCM (20 mL) was added dropwise DMSO (1.95 mL) [AT-78 °C.] The mixture was stirred at-78 °C for 30 min and a solution of the diol (1.00 g, 4.607 [MMOL)] was added dropwise. The reaction mixture was stirred for 2 hr and TEA (11.5 mL) was added. The reaction mixture was warmed to rt and water was added. The organic layer was separated and washed with sat. NaCl, dried over Na2SO4, and concentrated under reduced pressure to give [4-BROMO-BENZENE-1,] 2- dicarbaldehyde as a yellow oil (0.450 g, 46percent). A mixture of [4-BROMO-BENZENE-1,] [2-DICARBALDEHYDE] (0.450 g, 2.137 mmol), diethylamino malonate (0.452 g, 2.137 mmol), and sodium ethoxide (0.218 g, 3.20 [MMOL)] in anhydrous ethanol (15 mL) was refluxed for 4 hr. The solution was cooled to rt and concentrated under reduced pressure. The crude residue was purified by flash column chromatography (silica gel, 0. 5percent MeOH in [CHCI3)] to obtain 0.460 g (78percent) of the [7-BROMO-] isoquinoline-3-carboxylic acid ethyl ester which was [HYDROLYZED] according to general procedure C yielding the 0.350 g (85percent) of 7-bromo-isoquinoline-3-carboxylic acid as a white solid. LC/MS [(M/Z)] : 253 (M+1) [+.] [(2S)-AMINO-3-BIPHENYL-4YL-PROPIONIC] acid methyl ester (340 mg, 13.9 [MMOL)] was reacted with 7-bromo-isoquinoline-3-carboxylic acid (350 mg, 13.9 [MMOL)] as described in general procedure A. The resulting compound was hydrolyzed by following general procedure C yielding the title compound (132 mg, 81 percent) as a white solid
Reference: [1] Patent: WO2004/14844, 2004, A2, . Location in patent: Page 179; 185-186
[2] Patent: WO2018/15879, 2018, A1, . Location in patent: Page/Page column 85-86
  • 2
  • [ 13209-32-0 ]
  • [ 660830-62-6 ]
YieldReaction ConditionsOperation in experiment
78% With sodium ethanolate In ethanol for 4 h; Heating / reflux To a solution of 4-bromophthalic acid (3.0 g, 12.24 [MMOL)] in 30 mL of THF was added a solution of borane-THF complex (1. OM) dropwise at 0 [°C.] The solution was warmed to rt and stirred for 3 h. The reaction mixture was quenched by addition of HCI (2N) at 0 [°C.] The product was extracted with ethyl acetate and washed with sat. [NACI,] dried over [NA2SC4,] and concentrated under reduced pressure to afford 2.8 g (100percent) of 4-bromo-2- hydroxymethylbenzyl alcohol as a [COLORLESS OIL.APOS;H] NMR [(CDCK)] 7.28 (m, 2 H), 7.26 (m, 1 H), 4.69 (s, 4 H), 2.80 (bs, [2 H).] To a solution of oxalyl chloride (2.37 mL, 4.607 mmol) in DCM (20 mL) was added dropwise DMSO (1.95 mL) [AT-78 °C.] The mixture was stirred at-78 °C for 30 min and a solution of the diol (1.00 g, 4.607 [MMOL)] was added dropwise. The reaction mixture was stirred for 2 hr and TEA (11.5 mL) was added. The reaction mixture was warmed to rt and water was added. The organic layer was separated and washed with sat. NaCl, dried over Na2SO4, and concentrated under reduced pressure to give [4-BROMO-BENZENE-1,] 2- dicarbaldehyde as a yellow oil (0.450 g, 46percent). A mixture of [4-BROMO-BENZENE-1,] [2-DICARBALDEHYDE] (0.450 g, 2.137 mmol), diethylamino malonate (0.452 g, 2.137 mmol), and sodium ethoxide (0.218 g, 3.20 [MMOL)] in anhydrous ethanol (15 mL) was refluxed for 4 hr. The solution was cooled to rt and concentrated under reduced pressure. The crude residue was purified by flash column chromatography (silica gel, 0. 5percent MeOH in [CHCI3)] to obtain 0.460 g (78percent) of the [7-BROMO-] isoquinoline-3-carboxylic acid ethyl ester which was [HYDROLYZED] according to general procedure C yielding the 0.350 g (85percent) of 7-bromo-isoquinoline-3-carboxylic acid as a white solid. LC/MS [(M/Z)] : 253 (M+1) [+.] [(2S)-AMINO-3-BIPHENYL-4YL-PROPIONIC] acid methyl ester (340 mg, 13.9 [MMOL)] was reacted with 7-bromo-isoquinoline-3-carboxylic acid (350 mg, 13.9 [MMOL)] as described in general procedure A. The resulting compound was hydrolyzed by following general procedure C yielding the title compound (132 mg, 81 percent) as a white solid
Reference: [1] Patent: WO2004/14844, 2004, A2, . Location in patent: Page 185-186
  • 3
  • [ 13209-32-0 ]
  • [ 13433-00-6 ]
  • [ 660830-62-6 ]
YieldReaction ConditionsOperation in experiment
28% With sodium ethanolate In ethanol at 80℃; for 4 h; Inert atmosphere To a stirred solution of 4-bromophthalaldehyde (1 .6 g, 7.74 mmol, 1 .0 equiv) in ethanol (20 mL) was added diethyl 2-aminomalonate hydrochloride (1 .63 g, 7.74 mmol, 1 .0 equiv) and sodium ethoxide (3.9 mL, 1 1 .61 mmol, 1 .5 equiv) at room temperature, and the mixture was stirred for 4 h under nitrogen atmosphere at 80°C. The reaction mixture was cooled to room temperature and quenched with saturated ammonium chloride. The reaction mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic layers was dried over sodium sulphate and evaporated to obtain crude product. (0714) Run 2; To a stirred solution of 4-bromophthalaldehyde (1 .6 g, 7.74 mmol, 1 .0 equiv) in ethanol (20 mL) was added diethyl 2-aminomalonate hydrochloride (1 .63 g, 7.74 mmol, 1 .0 equiv) and sodium ethoxide (3.9 mL, 1 1 .61 mmol, 1 .5 equiv) at room temperature, and the mixture was stirred for 4 h under nitrogen atmosphere at 80°C. The reaction mixture was cooled to room temperature, and quenched with saturated ammonium chloride. The reaction mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic layers was dried over sodium sulphate and evaporated to obtain crude product. The crude products from Run 1 and Run 2 were combined and purified by silica gel flash column chromatography. The compound eluted out in 15 -25 percent EtOAc: Hexanes. The fractions were evaporated to obtain ethyl 7-bromoisoquinoline-3-carboxylate (1 .2 g, 28percent) as brown solid. 1 H NMR (400 MHz, CDCI3) δ ppm 1 .49 (t, J=7.2 Hz, 3 H), 4.51 - 4.57 (m, 2H), 7.86 (s, 2H), 8.24 (s, 1 H), 8.56 (s, 1 H), 9.28 (s, 1 H).
Reference: [1] Patent: WO2018/15879, 2018, A1, . Location in patent: Page/Page column 85
  • 4
  • [ 14091-15-7 ]
  • [ 660830-62-6 ]
Reference: [1] Patent: WO2014/121062, 2014, A1,
[2] Patent: US2017/240535, 2017, A1,
[3] Patent: US2018/141923, 2018, A1,
  • 5
  • [ 100129-12-2 ]
  • [ 660830-62-6 ]
Reference: [1] Patent: WO2014/121062, 2014, A1,
[2] Patent: US2017/240535, 2017, A1,
[3] Patent: US2018/141923, 2018, A1,
  • 6
  • [ 6968-28-1 ]
  • [ 660830-62-6 ]
Reference: [1] Patent: WO2018/15879, 2018, A1,
  • 7
  • [ 171011-37-3 ]
  • [ 660830-62-6 ]
Reference: [1] Patent: WO2018/15879, 2018, A1,
Historical Records

Related Functional Groups of
[ 660830-62-6 ]

Bromides

Chemical Structure| 1416713-22-8

[ 1416713-22-8 ]

6-Bromoisoquinoline-3-carboxylic acid

Similarity: 0.90

Chemical Structure| 474710-78-6

[ 474710-78-6 ]

Methyl 6-bromoquinazoline-4-carboxylate

Similarity: 0.80

Chemical Structure| 220844-77-9

[ 220844-77-9 ]

Ethyl 6-bromoquinoline-4-carboxylate

Similarity: 0.76

Chemical Structure| 481054-89-1

[ 481054-89-1 ]

Ethyl 6-bromoquinoline-3-carboxylate

Similarity: 0.74

Chemical Structure| 162102-79-6

[ 162102-79-6 ]

Dimethyl 4-bromopyridine-2,6-dicarboxylate

Similarity: 0.73

Esters

Chemical Structure| 27104-73-0

[ 27104-73-0 ]

Methyl isoquinoline-3-carboxylate

Similarity: 0.82

Chemical Structure| 474710-78-6

[ 474710-78-6 ]

Methyl 6-bromoquinazoline-4-carboxylate

Similarity: 0.80

Chemical Structure| 50458-79-2

[ 50458-79-2 ]

Ethyl 3-isoquinolinecarboxylate

Similarity: 0.79

Chemical Structure| 220844-77-9

[ 220844-77-9 ]

Ethyl 6-bromoquinoline-4-carboxylate

Similarity: 0.76

Chemical Structure| 481054-89-1

[ 481054-89-1 ]

Ethyl 6-bromoquinoline-3-carboxylate

Similarity: 0.74

Related Parent Nucleus of
[ 660830-62-6 ]

Isoquinolines

Chemical Structure| 1416713-22-8

[ 1416713-22-8 ]

6-Bromoisoquinoline-3-carboxylic acid

Similarity: 0.90

Chemical Structure| 27104-73-0

[ 27104-73-0 ]

Methyl isoquinoline-3-carboxylate

Similarity: 0.82

Chemical Structure| 50458-79-2

[ 50458-79-2 ]

Ethyl 3-isoquinolinecarboxylate

Similarity: 0.79

Chemical Structure| 203626-75-9

[ 203626-75-9 ]

Isoquinoline-3-carboxylic acid hydrate

Similarity: 0.74

Chemical Structure| 1455091-10-7

[ 1455091-10-7 ]

Methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Similarity: 0.72