Boron tribromide → 5-Chloro-7-(2-fluoro-4-iodo-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid

HRID 450122Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]([Cl:23])=[C:7]2[CH:12]=[CH:11][N:10]=[CH:9][N:8]2[C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22])=[O:4].B(Br)(Br)Br>C(Cl)Cl>[Cl:23][C:6]1[C:5]([C:3]([OH:4])=[O:2])=[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[F:22])[N:8]2[C:7]=1[CH:12]=[CH:11][N:10]=[CH:9]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-chloro-7-(2-fluoro-4-iodo-phenylamino)-pyrrolo[1,2-c]pyrimidine-6-carboxylic acid methyl ester (300 mg, 0.67 mmol) in DCM (6 mL) was added boron tribromide (0.65 mL, 6.7 mmol). The reaction was heated at reflux for 1 hour. The reaction mixture was cooled to 0° C. and carefully quenched by the addition of water (5 mL). The reaction mixture was diluted with aqueous hydrochloric acid (2 mL, 1M) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo to give the product as a dark brown solid (335 mg, 115%). LCMS (Method B): RT=3.58 min, M+H+=432.

Workup

temperatureThe reaction was heated
temperatureat reflux for 1 hour
customcarefully quenched by the addition of water (5 mL)
additionThe reaction mixture was diluted with aqueous hydrochloric acid (2 mL, 1M)
extractionextracted with ethyl acetate (3×10 mL)
washThe combined organic fractions were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c8edf95a09bb46c4a41384c89b85ce1a
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486963B2

Reaction notes

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