Dichloromethane → 3-fluoro-2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

HRID 2234640Notes

Reaction equation

HRID 2234640 reaction equation
[NH2:1][C:2]1[C:12]([F:13])=[CH:11][C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][N:20]([S:31]([C:34]4[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=4)(=[O:33])=[O:32])[C:17]3=[N:18][CH:19]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].ClCCl.[C:44](=O)(O)[O-:45].[Na+].C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[F:13][C:12]1[C:2]([N:1]=[C:44]=[O:45])=[C:3]([CH:9]=[C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][N:20]([S:31]([C:34]4[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=4)(=[O:32])=[O:33])[C:17]3=[N:18][CH:19]=2)[CH:11]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 577314782-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Product 1

HCID 577314603-fluoro-2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a scintillation vial was combined 125 mg (0.224 mmol) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide, 2.0 mL dichloromethane, and 2.0 mL of a saturated aqueous solution of sodium bicarbonate. The vial was cooled to 0° C. in an ice bath and, under vigorous stirring, 601 μL (1.12 mmol) of a 20% phosgene in toluene solution was added. The reaction was stirred in the ice bath for 30 minutes and then stirred at room temperature for another 30 minutes. The layers were separated and organic layer was dried over sodium sulfate and concentrated to afford 3-fluoro-2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a brown foam.

Workup

  1. additionwas added
  2. customThe layers were separated
  3. dry with materialorganic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f5819305c294274a02122608851ca85
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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