HCID 88019357, compound → HCID 23518945, compound

HRID 2416272Notes

Reaction equation

HRID 2416272 reaction equation
[C:1]([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)#[N:2].C(C1C=C2C(=CC=1)N(S(C1C=CC(C)=CC=1)(=O)=O)C=C2[C@@H]1C[C@H]1C=O)#N>>[C:1]([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:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 88019357HCID 88019357, compoundHCID 88043241rel-3-[(1R,2R)-2-Formylcyclopropyl]-1-[(4-methylphenyl)sulfonyl]-1H-indole-5-carbonitrile

Product 1

HCID 23518945HCID 23518945, compoundYield 37%

Procedure

Racemic [trans-2-[6-cyano-1-(p-toluenesulfonyl)indol-3-yl]-cyclopropane carboxaldehyde was prepared in a 37% yield from racemic [trans-2-[6-cyano-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) 9.11 (1H, d, J=5.5 Hz), 8.33 (1H, d, J=1.0 Hz), 7.99 (3H, m), 7.88 (1H, d, J=8.1 Hz), 7.69 (1H, dd, J=8.2, 1.4 Hz), 7.41 (2H, d, J=8.0 Hz), 2.76 (1H, m), 2.33 (3H, s), 2.14 (1H, m), 1.70 (2H, m); MS m/e 363 (M−H)−. Anal calcd. for C20H16N2O3S: C, 65.91; H, 4.42; N, 7.68. Found: C, 65.91; H, 4.45; N, 7.47.

Sources & evidence

ORD record
ord-08a323ce2ca84e1faee76c4a7b6278d9
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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