3-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfonyl)methyl]-1H-indole → 3-[Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-7-[(methylsulfonyl)methyl]-1H-indole

HRID 561674Notes

Reaction equation

HRID 561674 reaction equation
C1(C(C2C=CC3[O:21][C:22]([F:25])([F:24])[O:23]C=3C=2)C2C3C(=C(CSC)C=CC=3)NC=2)CC1.Cl[C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH:50]2[CH2:52][CH2:51]2)[C:36]2[C:44]3[C:39](=[C:40]([CH2:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:41]=[CH:42][CH:43]=3)[NH:38][CH:37]=2)=[CH:31][CH:30]=1>>[CH:50]1([CH:35]([C:32]2[CH:33]=[CH:34][C:29]3[O:21][C:22]([F:25])([F:24])[O:23][C:30]=3[CH:31]=2)[C:36]2[C:44]3[C:39](=[C:40]([CH2:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:41]=[CH:42][CH:43]=3)[NH:38][CH:37]=2)[CH2:52][CH2:51]1

Participants

3

Reactant 2

HCID 583920863-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfonyl)methyl]-1H-indoleHCID 583923293-[Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

Product 1

HCID 583921423-[Cyclopropyl(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-7-[(methylsulfonyl)methyl]-1H-indole

Procedure

The title compound was prepared starting from 500 mg (1.29 mmol) of the compound from Example 231 in analogy to the synthesis of the compound from Example 249. A difference was that the reaction solution was washed with saturated aqueous sodium bicarbonate solution before purification. 311 mg (57% of theory) of the target compound were obtained.

Workup

  1. washwas washed with saturated aqueous sodium bicarbonate solution before purification
  2. custom311 mg (57% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-0634e8819da34e8e9df21eeb8469b84c
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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