[ CAS No. 220239-67-8 ]

Name: 220239-67-8|2-(2-(Trifluoromethoxy)phenyl)acetic acid|98%
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Product Details of [ 220239-67-8 ]

CAS No. :	220239-67-8	MDL No. :	MFCD00236325
Formula :	C₉H₇F₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QFLBBLZROQPTAI-UHFFFAOYSA-N
M.W :	220.15	Pubchem ID :	2777313
Synonyms :

Safety of [ 220239-67-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 220239-67-8 ]

* 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 [ 220239-67-8 ]

[ 220239-67-8 ] Synthesis Path-Downstream 1~26

1
[ 220239-67-8 ]
[ 929612-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 0.833333h; Heating;

Reference： [1]Kanuma, Kosuke; Omodera, Katsunori; Nishiguchi, Mariko; Funakoshi, Takeo; Chaki, Shigeyuki; Nagase, Yasuko; Iida, Izumi; Yamaguchi, Jun-ichi; Semple, Graeme; Tran, Thuy-Anh; Sekiguchi, Yoshinori [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 10, p. 3307 - 3319]

2
[ 220239-67-8 ]
[ 509143-10-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride; DMF / CH₂Cl₂ / 0.83 h / Heating 2: 396 mg / iPr₂NEt / CH₂Cl₂ / 5 h / 4 °C

3
[ 220239-67-8 ]
N⁴,N⁴-dimethyl-N²-{cis-4-[({2-[2-(trifluoromethoxy)phenyl]ethyl}amino)methyl]cyclohexyl}quinazoline-2,4-diamine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride; DMF / CH₂Cl₂ / 0.83 h / Heating 2: 396 mg / iPr₂NEt / CH₂Cl₂ / 5 h / 4 °C 3: 81 mg / BH₃*THF / tetrahydrofuran / 2.5 h / Heating

4
[ 220239-67-8 ]
[ 170929-98-3 ]
[ 7732-18-5 ]
[ 75-05-8 ]
1-(2-trifluoromethoxyphenylacetyl)-2-carbamoyl-4-(2-methylphenyl)-piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In ethyl acetate; N,N-dimethyl-formamide	10.5 1-(2-trifluoromethoxyphenylacetyl)-2-carbamoyl-4-(2-methylphenyl)-piperazine STR20 Step 5. To a stirred solution of 2-trifluoromethoxyphenylacetic acid (0.10 g, 0.48 mmol) from Step 4 above and 2-carbamoyl-4-(2-methylphenyl)piperazine (0.10 g, 0.46 mmol) from Step 4 of Example 1 in DMF (10 mL) was added HOBT (0.075 g, 0.5 mmol), EDC (0.22 g, 0.75 mmol), and DIEA (0.13 mL, 0.75 mmol). The solution was stirred at ambient temperature for 14 h and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (50 mL) and 0.25 M aqueous citric acid (25 mL). The organic phase was separated and washed with H2 O (25 mL), saturated aqueous NaHCO3 (25 mL), and brine (25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using EtOAc as eluant. The product-containing fractions were evaporated under reduced pressure and the residue was lyophilized from CH3 CN:H2 O to give the title compound as an amorphous solid. HPLC retention time=9.1 min (method A) TLC Rf =0.2 (5:95 MeOH:CH2 Cl2); FAB MS: m/z=422 (M+ +H); combustion analysis: C21 H22 F3 N3 O3, 0.3 H2 O, 0.1 CH3 CN; Calculated C, 59.08; H, 5.36; N, 10.08; Found C, 59.10; H, 5.30; N, 10.17

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5968938, 1999, A

5
[ 137218-25-8 ]
[ 220239-67-8 ]

Yield	Reaction Conditions	Operation in experiment
	With concentrated aqueous HCl; acetic acid	10.4 1-(2-trifluoromethoxyphenylacetyl)-2-carbamoyl-4-(2-methylphenyl)-piperazine STR20 Step 4. 2-Trifluoromethoxyphenylacetonitrile (0.49 g, 2.6 mmol) from Step 3 above was refluxed for 3 h in a 1:1 mixture of acetic acid and concentrated aqueous HCl. The solvents were removed under reduced pressure. The residue was partitioned between EtOAc (75 mL) and water (2*25 mL). The organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure to give 2-trifluoromethoxyphenylacetic acid as an amorphous solid (HPLC retention time=6.8 min (method A)).
	With concentrated aqueous HCl; acetic acid	15.4 1-(1-(2-trifluoromethoxyphenylacetyl)piperidin-4-yl)-4H-3,1-benzoxazin-2(1H)-one STR30 Step 4. 2-Trifluoromethoxyphenylacetonitrile (0.49 g, 2.6 mmol) from Step 3 above was refluxed for 3 h in a 1:1 mixture of acetic acid and concentrated aqueous HCl. The solvents were removed under reduced pressure. The residue was partitioned between EtOAc (75 mL) and water (2*25 mL). The organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure to give 2-trifluoromethoxyphenylacetic acid as an amorphous solid (HPLC retention time=6.8 min (method A)).

Reference： [1]Current Patent Assignee: MERCK & CO INC - US5968938, 1999, A
[2]Current Patent Assignee: MERCK & CO INC - US6090805, 2000, A

6
[ 220239-67-8 ]
[ 32776-22-0 ]
[ 1030630-28-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 2-[2-(trifluoromethoxy)phenyl]acetic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Stage #2: 1-(2-methylaminoethyl)pyrrolidine In dichloromethane at 20℃; for 0.333333h;

Reference： [1]Location in patent: experimental part Smith, Trudy A.; Yang, Xiaowen; Wu, Huifang; Pouw, Buddy; Matsumoto, Rae R.; Coop, Andrew [Journal of Medicinal Chemistry, 2008, vol. 51, # 11, p. 3322 - 3325]

7
[ 220239-67-8 ]
[ 41239-39-8 ]
[ 1030630-30-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 2-[2-(trifluoromethoxy)phenyl]acetic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Stage #2: N-methyl-2-(piperidin-1-yl)ethanamine In dichloromethane at 20℃; for 0.333333h;

8
[ 220239-67-8 ]
[ 32776-21-9 ]
[ 1030630-31-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: 2-[2-(trifluoromethoxy)phenyl]acetic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Stage #2: N-ethyl-N-(2-piperidin-1-ylethyl)amine In dichloromethane at 20℃; for 0.333333h;

9
[ 220239-67-8 ]
[ 138356-55-5 ]
[ 1030630-29-5 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 3322 - 3325

10
[ 220239-67-8 ]
[ 64-17-5 ]
[ 1159678-02-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With thionyl chloride at 0 - 50℃; for 12h;	1A Example 1A20.0 g (90.9 mmol) of (2-trifluoromethoxy-phenyl)-acetic acid were dissolved in 150 ml of absolute ethanol. At 00C 10.0 ml (138 mmol) of thionylchloride were slowly added. The solution was heated to 500C for 12 h. Cooling to room temperature was followed by evaporation of the solvent under reduced pressure. The remaining residue was dissolved in 10 ml of ethyl acetate and filtered through a pad of activated basic alumina. The ester was obtained as a colourless oil (18.4 g, 81 % of theory).HPLC-MS (Method 1 ): RT: 1.64 min MS (ESI pos): m/z = 249 (M+H)+.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2009/68617, 2009, A1 Location in patent: Page/Page column 53

11
[ 220239-67-8 ]
[ 1159679-04-5 ]
[ 1159677-92-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With PPA at 120℃; for 24h;	32 Example 32Example 9C (0.15g; 0.65 mmol) was suspended in a 50 ml flask with polyphosphoric acid (1g) and 2-(thfluoromethoxy)phenylacetic acid (428 mg; 1.94 mmol). The mixture, under mechanic stirring, was heated at 1200C during 24 hours and the temperature was then lowered at room temperature, water was added (10 ml) and pH value was adjusted to 7 by addition of NH4OH (30% solution). The aqueous phase was extracted with CH2CI2 (2x20ml) and the organic phase was dried over sodium sulphate. The crude product was purified by flash chromatography. Eluent: hexane/ethyl acetate 30/70.Obtained 40mg (0.09 mmol; yield = 34%) of the desired compound LC-MS (Method 1 E): RT = 8.35 min MS (APCI): m/z = 456 (M+H)

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2009/68617, 2009, A1 Location in patent: Page/Page column 90-91

12
[ 220239-67-8 ]
[ 530-62-1 ]
C₁₃H₉F₃N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; triethylamine In ISOPROPYLAMIDE at 20℃; for 2h; Inert atmosphere;

Reference： [1]DeNinno, Michael P.; Andrews, Melissa; Bell, Andrew S.; Chen, Yue; Eller-Zarbo, Cynthia; Eshelby, Nan; Etienne, John B.; Moore, Dianna E.; Palmer, Michael J.; Visser, Michael S.; Yu, Li J.; Zavadoski, William J.; Michael Gibbs [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 9, p. 2537 - 2541]

13
[ 220239-67-8 ]
[ 494769-44-7 ]
[ 1363397-20-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 8h;	General procedure: The intermediate (3) (0.5 g, 0.00217 mol), EDCl (0.622 g, 0.00325 mol), DMAP (0.345 g, 0.0028 mol) were stirred in dichloromethane (6 mL) at 0 C, and the substituted acid (0.00217 mol) were dissolved in (4 mL) of dichloromethane and charged to the reaction mixture and stirred at room temperature for 8 h. The reaction completion was monitored by TLC. Reaction was completed. The reaction mixture was diluted with (10 mL) of dichloromethane, and was washed with 10% NaHCO3 (10 mL). Separated the organic layer and was washed with saturated brine solution (10 mL). The organic layer was dried over sodium sulfate and concentrated the organic layer under reduced pressure to afford compounds 4a-t. The spectral data of compounds 4(a-t) are given below.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 49,p. 172 - 182

14
[ 220239-67-8 ]
[ 109-70-6 ]
[ 1262107-19-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 2-[2-(trifluoromethoxy)phenyl]acetic acid With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 1.3-chlorobromopropane In tetrahydrofuran; hexane at 20℃; for 16h;	22.22a To a solution of [2-(trifluoromethoxy)phenyl]acetic acid (2.52 g, 11.4 mmol) in THF (50 mL) was added dropwise n-butyllithium 1.6 M hexane solution (14.3 mL, 22.9 mmol) at - 78°C, and the mixture was stirred under ice-cooling for 2 hr. 1-Bromo-3-chloropropane (12.0 mmol, 1.18 mL) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was extracted with 1 M aqueous sodium hydroxide solution. The extract was acidified with 3 M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/80 - 50/50) to give the title compound as a colorless oil (2.71 g, 87%). 1H NMR (CDCl3) δ: 1. 58 - 2.01 (3 H, m), 2. 15 - 2.32 (1 H, m), 3.52 (2 H, t, J=6.4 Hz), 4.03 (1 H, t, J=7.5 Hz), 7.23 - 7.37 (3 H, m), 7.41 - 7.48 (1 H, m).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2455380, 2012, A1 Location in patent: Page/Page column 82

15
[ 220239-67-8 ]
[ 1262106-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C 1.2: 16 h / 20 °C 2.1: triethylamine; diethyl dicarbonate / N,N-dimethyl-formamide / 17 h / 20 °C 2.2: 2 h / 80 °C 3.1: sodium azide / dimethyl sulfoxide / 15.5 h / 70 °C 3.2: 2 h / 60 °C 3.3: 2 h / 130 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2455380, 2012, A1

16
[ 220239-67-8 ]
[ 1262107-18-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C 1.2: 16 h / 20 °C 2.1: triethylamine; diethyl dicarbonate / N,N-dimethyl-formamide / 17 h / 20 °C 2.2: 2 h / 80 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2455380, 2012, A1

17
[ 220239-67-8 ]
[ 1262106-53-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 °C 1.2: 16 h / 20 °C 2.1: triethylamine; diethyl dicarbonate / N,N-dimethyl-formamide / 17 h / 20 °C 2.2: 2 h / 80 °C 3.1: sodium azide / dimethyl sulfoxide / 4 h / 70 °C 3.2: 3.5 h / 60 °C 3.3: 1 h / Reflux

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP2455380, 2012, A1

18
[ 220239-67-8 ]
6-[(3R)-3-(pyridazin-3-ylamino)pyrrolidin-1-yl]pyridazin-3-amine [ No CAS ]
N-[6-[(3R)-3-(pyridazin-3-ylamino)pyrrolidin-1-yl]pyridazin-3-yl]-2-[2-(trifluoromethoxy)phenyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 17 - 30℃; for 15h; Inert atmosphere;	6 Example 6 3- ylamino)pyrrolidin-l-yl]pyridazin-3-amine (Intermediate 1, 0.04 g, 0.159 mmol) were weighed into a round bottom flask. DMF (1 mL) and HATU (0.06 g, 0.159 mmol) were added and stirred for 5 mins to effect dissolution. Then DIPEA (0.05 g, 0.398 mmol) was added in one portion and the mixture was allowed to stir at room temperature for 15 hours. The solvent was removed under reduced pressure and was absorbed onto silica and purified by flash column chromatography gradient eluting with 100% DCM up to 10% methanolic ammonia: 90% DCM to elute the title compound as a pale yellow solid (50 mg). LCMS analysis showed that there was a 5% impurity of hydroxy benzotriazole (HOBt). The solid was dissolved in DMSO (1 mL) and purified by mass directed LCMS (Waters C18 SunFire column, 5 μιη pore size, 4.60 mm diameter, 50 mm length). The flow rate was 25 mL/min and the mobile phases of water and acetonitrile contained 0.1% formic acid. The elution was started at 95% water: 5% acetonitrile which was held for 1.5 minutes ramping up to 5% water:95% acetonitrile over 10 minutes. This was then held for 30 seconds, such that the complete length of the run was 12 minutes. The appropriate fractions were added to an SCX cartridge and washed with methanol, and then the title compound was eluted with 2M ammonia in methanol. The solvent was evaporated under reduced pressure to provide N-[6-[(3R)-3-(pyridazin-3-ylamino)pyrrolidin-l-yl]pyridazin-3-yl]-2- [2-(trifluoromethoxy)phenyl]acetamide as a white solid (0.038 g, 51%). (0228) XH NMR (400 MHz, DMSO, 21.8°C) δ 2.01 - 2.08 (IH, m), 2.28 - 2.37 (IH, m), 3.42 (dd, IH), 3.52 - 3.64 (m, 2H), 3.81 (dd, IH), 3.85 (s, 2H), 4.60 - 4.63 (m, IH), 6.81 (dd, IH), 6.98 (d, IH), 7.13 (d, IH), 7.24 (dd, IH), 7.32 - 7.43 (m, 3H), 7.47 - 7.49 (m, IH) 7.95 (d, IH), 8.45 (dd, IH), 10.90 (s, IH); m/z: ES+ [M+H]+ 460.

Reference： [1]Current Patent Assignee: CANCER RESEARCH UK - WO2017/89587, 2017, A1 Location in patent: Page/Page column 25-26

19
[ 220239-67-8 ]
5-[2-(benzyloxy)-4-fluorophenyl]-1,3,9-triazaspiro[5.5]undecan-2-one hydrochloride [ No CAS ]
5-[2-(benzyloxy)-4-fluorophenyl]-9-[2-(trifluoromethoxy)phenyl]acetyl}-1,3,9-triazaspiro[5.5]undecan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
560 mg	With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 17h;	14 Intermediate 14: (5R)-5-[2-(benzyloxy)-4-fluorophenyl]-9-[2-(trifluoromethoxy)phenyl]acetyl}-1,3,9- triazaspiro[5.5]undecan-2-one N,N-diisopropylethylamine (590 mI, 3.4 mmol), [2-(trifluoromethoxy)phenyl]acetic acid (205 mg, 930 mihoI; CAS-RN: 220239-67-8) and HATU (233 mI, 4.0 M, 930 gmol) were added to a solution of (5-[2-(benzyloxy)-4-fluorophenyl]-1,3,9-triazaspiro[5.5]undecan-2-one, salt with hydrochloric acid (343 mg, 846 mihoI, Intermediate 9) in DMF (10 ml) and the mixture was stirred for 17 h at room temperature. The reaction mixture was concentrated in vacuo. Purification by column chromatography using an Isolera system gave the title compound 560 mg. 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 0.798 (0.21), 0.815 (0.27), 0.822 (0.27), 0.886 (0.18), 0.905 (0.30), 0.933 (0.67), 0.950 (0.64), 1.071 (0.24), 1.138 (0.36), 1.154 (3.86), 1.172 (8.29), 1.190 (4.58), 1.228 (1.70), 1.251 (1.70), 1.289 (2.06), 1.319 (1.55), 1.352 (1.03), 1.383 (2.43), 1.413(1.46), 1.484(1.46), 1.518(1.18), 1.555(1.21), 1.587 (0.97), 1.987 (12.69), 2.518 (5.92), 2.523 (4.28), 2.729 (0.27), 2.888 (0.43), 2.928 (0.82), 2.957 (1.49), 2.985 (0.82), 3.114 (0.73), 3.143 (1.31), 3.204 (0.97), 3.228 (1.55), 3.282 (3.04), 3.309 (2.25), 3.380 (2.31), 3.394 (2.64), 3.411 (1.31), 3.430 (1.49), 3.445 (2.19), 3.460 (1.49), 3.487 (1.43), 3.517 (1.15), 3.565 (3.83), 3.605 (4.77), 3.634 (8.96), 3.706 (3.92), 3.746 (2.40), 3.899 (1.09), 3.955 (1.34), 3.988 (1.21), 4.000 (1.49), 4.017 (2.82), 4.035 (2.82), 4.053 (0.91), 5.050 (1.21), 5.079 (6.04), 5.090 (6.01), 5.128 (8.20), 5.160 (0.36), 6.426 (4.98), 6.649 (7.56), 6.751 (1.12), 6.758 (1.49), 6.772 (2.55), 6.779 (3.01), 6.790 (2.46), 6.800 (1.67), 6.811 (1.12), 7.027 (2.16), 7.035 (3.55), 7.043 (2.52), 7.057 (2.37), 7.064 (3.55), 7.071 (2.28), 7.185 (0.49), 7.209 (5.56), 7.218 (10.72), 7.226 (8.11), 7.231 (6.95), 7.248 (8.41), 7.268 (5.98), 7.324 (1.49), 7.331 (3.55), 7.336 (3.49), 7.346 (7.01), 7.354 (5.86), 7.363 (6.71), 7.367 (6.01), 7.376 (4.19), 7.385 (4.80), 7.397 (9.62), 7.405 (14.21), 7.411 (16.00), 7.421 (5.28), 7.438(6.41), 7.455(2.85). LC-MS (Method 9: Rt = 1.27 min; MS (ESIpos): m/z = 572 [M+H]+

Reference： [1]Current Patent Assignee: BAYER AG - WO2020/48827, 2020, A1 Location in patent: Page/Page column 148-149

20
[ 220239-67-8 ]
2-[2-(trifluoromethoxy)phenyl]ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 0.666667h; Inert atmosphere;	38.1 Step 1: 2-[2-(trifluoromethoxy )phenyl]ethan-l-ol A solution of 2-[2- (trifluoromethoxy)pheny 1] acetic acid (2.5 g, 11 mmol, 1.0 eq) in anhydrous THF (6 mL) at 0°C was added dropwise to a lithium aluminium hydride solution (2 M solution in THF, 23 mmol, 11 mL,) under argon atmosphere. The reaction was exothermic and the mixture became yellow. The reaction mixture was stirred for 40 min at room temperature, cooled to 0°C and then quenched slowly with 0.86 mL of HhO. A 15% aqueous solution of NaOH (0.86 mL) and H2O (2.6 mL) were successively added and the mixture was stirred for 15 min. Anhydrous Na2S04 was added and the mixture was stirred for 15 min. The yellow mixture was filtered over a pad of celite and the filtrate was concentrated under vacuum. The mixture was concentrated and purified by column chromatography to afford the desired intermediate (2 g, 85%) as a clear oil. (0977) MS (ESI+): [M+H = 207.2 (0978) NMR (CDCls, 500 MHz) d (ppm): 7.35 - 7.31 (m, 1H); 7.29 - 7.21 (m, 3H); 3.87 (t, 3 = 6.8 Hz, 2H); 2.96 (t, J = 6.7 Hz, 2H); 1.46 (s, 1H)

Reference： [1]Current Patent Assignee: QUANTUM GENOMICS SA; COLLEGE DE FRANCE; NATIONAL INSTITUTE OF HEALTH AND MEDICAL RESEARCH; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - WO2020/84131, 2020, A1 Location in patent: Page/Page column 81-82

21
[ 220239-67-8 ]
1-(2-bromoethyl)-2-(trifluoromethoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / -5 - 20 °C

22
[ 220239-67-8 ]
3-((dimethylamino)methyl)-4-(3-hydroxyphenyl)piperidin-4-ol hydrochloride [ No CAS ]
1-(3-((dimethylamino)methyl)-4-hydroxy-4-(3-hydroxyphenyl)piperidin-1-yl)-2-(2-(trifluoromethoxy)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34.8%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

Reference： [1]Huang, Huoming; Li, Xueping; Xie, Peng; Li, Xinwei; Xu, Xuejun; Qian, Yuanyuan; Yuan, Congmin; Meng, Xiangguo; Chai, Jingrui; Chen, Jing; Liu, Jing; Wang, Wenli; Li, Wei; Wang, Yujun; Fu, Wei; Liu, Jinggen [Journal of Medicinal Chemistry, 2021, vol. 64, # 13, p. 9458 - 9483]

23
[ 220239-67-8 ]
[ 143-16-8 ]
N,N-dihexyl-2-(2-(trifluoromethoxy)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1′-carbonyldiimidazole In dichloromethane at 20℃;	4.2 General procedure for synthesis of amides General procedure: In an unoptimized procedure9, a 50 mL flask was charged with a stir bar, substituted 2-phenylacetic acid (5.0 mmol), 2.3 g dihexylamine (12.5 mmol), 0.97 g CDI (6.0 mmol),and 20 mL DCM. The resulting mixture was allowed to stir at rt and monitored by TLC.Quenched with 1 N HCl aqueous and then extracted with DCM (20 mL × 3). Combinedorganics were washed with brine and dried over anhydrous Na2SO4, and all volatileswere removed in vacuo. This residue was purified by flash chromatography on silicagel (hexane/ethyl acetate = 20:1 to 5:1) to afford desired amide.

Reference： [1]Chang, Wenju; Chen, Yu; Lu, Shuo; Jiao, Hongyun; Wang, Yajun; Zheng, Tianyu; Shi, Zhuangzhi; Han, Yingbin; Lu, Yi; Wang, Yi; Pan, Yi; Yu, Jin-Quan; Houk, Kendall N.; Liu, Fang; Liang, Yong [Chem, 2022, vol. 8, # 6, p. 1775 - 1788]

24
[ 220239-67-8 ]
N,N-dihexyl-2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,1′-carbonyldiimidazole / dichloromethane / 20 °C 2: 1-(2-([2,2'-bipyridin]-4-yl)phenyl)-3-(2-adamantyl)urea; bis(η⁴-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I) / para-xylene / 24 h / 25 °C / Inert atmosphere; Glovebox; Sealed tube

25
[ 220239-67-8 ]
N,N-dihexyl-2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenyl)acetamide [ No CAS ]
N,N-dihexyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,1′-carbonyldiimidazole / dichloromethane / 20 °C 2: bis(η⁴-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I); 4,4′-di-tert-butyl-2,2′-bipyridine / para-xylene / 24 h / 25 °C / Inert atmosphere; Glovebox; Sealed tube

26
[ 220239-67-8 ]
N,N-dihexyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,1′-carbonyldiimidazole / dichloromethane / 20 °C 2: 1-(2'-(1,10-phenanthrolin-5-yl)-[1,1'-biphenyl]-4-yl)-3-(2-adamantyl)urea; bis(η⁴-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I) / para-xylene / 24 h / 25 °C / Inert atmosphere; Glovebox; Sealed tube

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[ CAS No. 220239-67-8 ]

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[ 220239-67-8 ] Synthesis Path-Downstream 1~26

Related Functional Groups of [ 220239-67-8 ]

Fluorinated Building Blocks

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[ 220239-67-8 ]