Iodine chloride → HCID 59703911, compound

HRID 1366792Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[C:12]([F:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Si](C)(C)C)=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2].[I:28]Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:14][C:13]2[C:12]([F:15])=[CH:11][N:10]=[CH:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:28])=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 7-fluoro-3-(2-fluoro-4-trimethylsilanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid ethyl ester (330 mg, 0.81 mmol) in DCM (10 mL) was added iodine monochloride (1M in DCM, 1.6 mL, 1.6 mmol) dropwise. On complete addition the mixture was allowed to stir at 0° C. for 1 hour then quenched by the addition of saturated sodium thiosulphate solution (10 mL). The mixture was stirred vigorously for 10 min and partitioned between ethyl acetate and water. The organic layer was separated and washed with a saturated solution of sodium hydrogenocarbonate followed by brine, dried over sodium sulphate, filtered and concentrated to give the title compound as a yellow solid (358 mg, 54%). LCMS (method B): RT=4.72 min, M+H+=461.

Workup

additionOn complete addition the mixture
customthen quenched by the addition of saturated sodium thiosulphate solution (10 mL)
stirringThe mixture was stirred vigorously for 10 min
custompartitioned between ethyl acetate and water
customThe organic layer was separated
washwashed with a saturated solution of sodium hydrogenocarbonate
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-3fe93f0e89f14191bfbd6fbaa5cc878a
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893085B2

Reaction notes

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