Benzyl chloroformate → HCID 71164798, compound

HRID 1622570Notes

Reaction equation

HRID 1622570 reaction equation
C([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:19]1[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)(C)C.CCN(C(C)C)C(C)C.ClC(O[CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=O>C(Cl)Cl>[CH2:40]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:19]1[C:24]([Br:25])=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:17])([F:16])[F:18])=[CH:13][CH:14]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 71164782(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate2×

Product 1

HCID 71164798HCID 71164798, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled solution of (S)-(3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine hydrochloride (Intermediate 40) (1.20 g, 2.2 mmol), DIPEA (1.50 mL, 8.6 mmol), and DCM (20 mL) was added benzyl chloroformate (0.40 mL, 2.8 mmol). The resulting mixture was allowed to warm to rt as the bath warmed. After 16 h, the reaction was eluted through a cartridge of silica gel (25 g) with DCM. The filtrate was concentrated in vacuo to give the title compound as a light yellow oil. MS (ESI pos. ion) m/z: 464.9, 466.9 (M+H).

Workup

  1. temperaturewarmed
  2. washthe reaction was eluted through a cartridge of silica gel (25 g) with DCM
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7a46b5251a5d44359a9b725c36eea9ec
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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