Methyl 3-iodobenzoate → HCID 58305409, compound

HRID 1805389Notes

Reaction equation

HRID 1805389 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 58305285(1S,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305409HCID 58305409, compound

Procedure

The title compound was prepared in analogy to Example 85 starting from methylsulfonamide, methyl-3-iodobenzoate (commercially available), (1R,2S) and (1S,2R)-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 2.15 (dd, J=9.09, 4.80 Hz, 1 H) 2.44 (dd, J=8.08, 4.80 Hz, 1 H) 3.25 (t, J=8.59 Hz, 1 H) 3.41 (s, 3 H) 6.21 (d, J=7.58 Hz, 1 H) 6.79-6.88 (m, 2 H) 7.10-7.17 (m, 1 H) 7.37-7.45 (m, 4 H) 7.75 (t, J=7.83 Hz, 1 H) 7.80-7.85 (m, 1 H) 8.04 (d, J=7.83 Hz, 1 H) 8.11-8.16 (m, 1 H) 12.29 (br. s., 1 H).

Sources & evidence

ORD record
ord-e5f6796fe69e4c3ab466a6b97bde81cb
Source dataset
uspto-grants-2013_01
Patent number
US08354443B2

Reaction notes

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