Chloroacetyl chloride → HCID 68172805, compound

HRID 713989Notes

Reaction equation

HRID 713989 reaction equation
[F:1][C:2]([F:20])([F:19])[CH:3]1[CH2:8][CH2:7][CH:6]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH2:14][CH2:13]3)[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[Cl:30][CH2:31][C:32](Cl)=[O:33]>C(Cl)Cl>[Cl:30][CH2:31][C:32]([N:15]1[C:16]2[C:12](=[CH:11][C:10]([O:9][CH:6]3[CH2:5][CH2:4][CH:3]([C:2]([F:1])([F:19])[F:20])[CH2:8][CH2:7]3)=[CH:18][CH:17]=2)[CH2:13][CH2:14]1)=[O:33]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 66926636HCID 66926636, compound

Product 1

HCID 68172805HCID 68172805, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-(4-trifluoromethyl-cyclohexyloxy)-2,3-dihydro-1H-indole (130 mg, 0.46 mmol) and DIEA (103 uL) in methylene chloride (2 mL) was added chloroacetyl chloride (47 uL, 0.59 mmol) at room temperature. The black solution was stirred for 30 min. The solvent was concentrated to give crude product. The crude was used directly for next step without further purification (80 mg, yield: 77%). ESI-MS: 362.10 (M+H)+.

Workup

  1. concentrationThe solvent was concentrated
  2. customto give crude product
  3. customThe crude was used directly for next step without further purification (80 mg, yield: 77%)

Sources & evidence

ORD record
ord-c7aab8e25eaf4c5082315afdcb4ef0b6
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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