HCID 66886812, compound → HCID 86649872, compound

HRID 2089053Notes

Reaction equation

HRID 2089053 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=2)[N:4]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:3]=1.[I:25][C:26]1[C:34]2[C:29](=[N:30][CH:31]=[C:32]([N:35]([S:40]([CH3:43])(=[O:42])=[O:41])[S:36]([CH3:39])(=[O:38])=[O:37])[CH:33]=2)[N:28]([S:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)(=[O:46])=[O:45])[CH:27]=1>>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([NH:11][S:12]([CH3:15])(=[O:13])=[O:14])[CH:9]=2)[N:4]([S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:3]=1.[I:25][C:26]1[C:34]2[C:29](=[N:30][CH:31]=[C:32]([N:35]([S:36]([CH3:39])(=[O:37])=[O:38])[S:40]([CH3:43])(=[O:41])=[O:42])[CH:33]=2)[N:28]([S:44]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)(=[O:46])=[O:45])[CH:27]=1

Participants

3

Reactant 2

HCID 66886812HCID 66886812, compoundHCID 66888546HCID 66888546, compound

Product 1

HCID 86649872HCID 86649872, compound

Procedure

To a suspension of Example 226a (118 mg, 0.23 mmol) in 4 mL dichloromethane was added triethylamine (0.64 mL, 4.6 mmol). The reaction flask was cooled in an ice bath and methanesulfonyl chloride (0.054 mL, 0.69 mmol) added. After stirring 10 minutes, the ice bath was removed and the reaction mixture stirred 2 days at room temperature. The solvent was evaporated to dryness to give a crude product that was a mixture of N-(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-yl)methanesulfonamide and N-(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-5-yl)-N-(methylsulfonyl)methansulfonamide that was carried on to the next step without purification.

Workup

  1. customwas carried on to the next step without purification

Sources & evidence

ORD record
ord-e90887ce5ca3476dabed3d78c00425b1
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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