Benzoyl chloride → HCID 15462189, compound

HRID 1870967Notes

Reaction equation

HRID 1870967 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]1([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[C:20]3[CH2:26][C@H:27]2[CH2:31][CH2:30][CH2:29][N:28]2[CH3:32])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH:10]1([O:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:21]=[C:20]3[CH2:26][C@H:27]2[CH2:31][CH2:30][CH2:29][N:28]2[CH3:32])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 53631894HCID 53631894, compound

Product 1

HCID 15462189HCID 15462189, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (0.10 mL, 0.86 mmol) was added to a solution of (R)-5-cyclohexyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indole (Example 3g, ~75 mg, 0.24 mmol), triethylamine (0.20 mL, 1.4 mmol) and DMAP (23 mg, 0.19 mmol) in dichloromethane (2.5 mL). The mixture was stirred for 15 h. prior to quenching with water (25 mL) and extraction into dichloromethane. The organic layer was washed with brine and dried over sodium sulfate. Purification by flash chromatography (silica gel, 2M methanolic ammonia in chloroform (1.5-3.3%) yielded (R)-5-cyclohexyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-benzoylindole (20.1 mg, 20%, HRMS-FAB+ for C27H32N2O2 : calculated MH+ :417.25421; found MH+ :417.25475).

Workup

  1. customto quenching with water (25 mL) and extraction into dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customPurification by flash chromatography (silica gel, 2M methanolic ammonia in chloroform (1.5-3.3%)

Sources & evidence

ORD record
ord-8374dc9e2a2a4774b2a9cc1a69e19d4b
Source dataset
uspto-grants-2000_08
Patent number
US06100291

Reaction notes

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