Sodium methanesulfinate → HCID 53245140, compound

HRID 1805351Notes

Reaction equation

HRID 1805351 reaction equation
[Na+].[CH3:2][S:3]([O-:5])=[O:4].Br[C:7]1[CH:8]=[C:9]([CH:13]=[C:14](I)[CH:15]=1)[C:10]([OH:12])=[O:11].[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:7]4[CH:8]=[C:9]([CH:13]=[C:14]([S:3]([CH3:2])(=[O:5])=[O:4])[CH:15]=4)[C:10]([OH:12])=[O:11])[C:27]3=[O:35])[CH2:25]2)=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 2733271Sodium methanesulfinateHCID 51825203-Bromo-5-iodobenzoic acidHCID 67232941(1S,2S)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 53245140HCID 53245140, compound

Procedure

The title compound was prepared in analogy to Example 92 starting from methanesulfinic acid sodium salt, 3-bromo-5-iodo-benzoic acid (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 C24H18ClNO55: 467, observed (M+H)+: 468.1 1H NMR (400 MHz, MeOD-d4) δppm 2.27-2.36 (m, 2 H) 3.28 (s, 3 H) 3.38 (t, J=8.59 Hz, 1 H) 6.18 (d, J=7.58 Hz, 1 H) 6.85 (t, J=7.20 Hz, 1 H) 7.00 (d, J=7.83 Hz, 1 H) 7.14-7.23 (m, 1 H) 7.28-7.40 (m, 4 H) 8.38 (t, J=1.89 Hz, 1 H) 8.49 (s, 1 H) 8.62 (s, 1 H).

Sources & evidence

ORD record
ord-e7a86b48ea9542e5bf267390e9e85e47
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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