HCID 88025256, compound → HCID 88043063, compound

HRID 1836645Notes

Reaction equation

HRID 1836645 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C@@H:22]3[CH2:24][C@H:23]3[C:25](N(OC)C)=[O:26])=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1.C(C1C=C2C(=CC=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2[C@@H]1C[C@H]1C=O)#N>>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C@@H:22]3[CH2:24][C@H:23]3[CH:25]=[O:26])=[CH:8][N:9]2[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 88025256HCID 88025256, compoundHCID 88043241rel-3-[(1R,2R)-2-Formylcyclopropyl]-1-[(4-methylphenyl)sulfonyl]-1H-indole-5-carbonitrile

Product 1

HCID 88043063HCID 88043063, compoundYield 89%

Procedure

Racemic [trans-2-[6-trifluoromethyl-1-(p-toluenesulfonyl)indol-3-yl]-cyclopropane-carboxaldehyde was prepared in an 89% yield from racemic [trans-2-[6-trifluoromethyl-1-(p-toluenesulfonyl)indol-3-yl]cycloprop-1-yl]-N-methoxy-N-methyl-carboxamide in a similar manner to [trans-2-[5-cyano-1-(p-toluenesulfonyl)indol-3-yl]cyclopropane-carboxaldehyde in Example 1. 1H NMR (400 MHz, DMSO-d6) 9.12 (1H, d, J=5.4 Hz), 8.15 (1H, s), 7.92 (4H, m), 7.64 (1H, dd, J=8.3, 1.1 Hz), 7.41 (2H, d, J=8.1 Hz), 2.78 (1H, m), 2.32 (3H, s), 2.15 (1H, m), 1.71 (2H, m); MS m/e 406 (M−H)−. Anal calcd. for C20H16F3NO3S: C, 58.96; H, 3.95; N, 3.43. Found: C, 58.93; H, 3.93; N, 3.25.

Sources & evidence

ORD record
ord-111f3b22c90444488bacf0ceff2d5b15
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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