Methyl 3-iodobenzoate → HCID 58305368, compound

HRID 1805347Notes

Reaction equation

HRID 1805347 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].CO[C:8](=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C@H:24]2[C@:26]3([C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:28][C:27]3=[O:35])[CH2:25]2)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C@H:24]2[C@:26]3([C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]([C:11]4[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=4)[C:8]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:16])[C:27]3=[O:35])[CH2:25]2)=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 69258Methyl 3-iodobenzoateHCID 72879MethanesulfonamideHCID 67232941(1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305368HCID 58305368, compound

Procedure

The title compound was prepared in analogy to Example 85 starting from methanesulfonamide, methyl-3-iodobenzoate (commercially available), (1R,2R) and (1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one prepared as in Scheme 1. LC/MS m/e calcd. for C24H19ClN2O4S: 466, observed (M+H)+: 467.2 1H NMR (400 MHz, DMSO-d6) δppm 2.31-2.41 (m, 2 H) 3.37 (s, 3 H) 3.43 (t, J=8.72 Hz, 1 H) 6.90 (d, J=7.83 Hz, 1 H) 7.16 (t, J=7.33 Hz, 1 H) 7.25 (dd, J=7.83, 1.01 Hz, 1 H) 7.27-7.35 (m, 3 H) 7.35-7.43 (m, 2H) 7.62-7.70 (m, 2 H) 7.94-7.99 (m, 2 H) 12.24 (br. s., 1 H).

Sources & evidence

ORD record
ord-dc9a024ae33f4f28a715a62a2865f29a
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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