HCID 88042769, compound → HCID 88042754, compound

HRID 2416267Notes

Reaction equation

HRID 2416267 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[C@@H:22]1[CH2:24][C@H:23]1[C:25](N(OC)C)=[O:26].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:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[C@@H:22]1[CH2:24][C@H:23]1[CH:25]=[O:26]

Participants

3

Reactant 2

HCID 88042769HCID 88042769, compoundHCID 88043241rel-3-[(1R,2R)-2-Formylcyclopropyl]-1-[(4-methylphenyl)sulfonyl]-1H-indole-5-carbonitrile

Product 1

HCID 88042754HCID 88042754, compoundYield 95%

Procedure

Racemic [trans-2-[5-trifluoromethyl-1-(p-toluenesulfonyl)indol-3-yl]-cyclo-propane-carboxaldehyde (4.13 g, 95%) was prepared from racemic [trans-2-[5-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) 9.06 (1H, d, J=5.7 Hz), 8.11 (2H, d, J=8.9 Hz), 7.89 (3H, m), 7.69 (1H, d, J=8.8 Hz), 7.40 (2H, d, J=8.0 Hz), 2.86 (1H, m), 2.32 (3H, s), 2.12 (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, 58.95; H, 3.96; N, 3.28

Sources & evidence

ORD record
ord-232c59647c0647fba79a4485f801a95c
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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