Boron tribromide → HCID 90413325, compound

HRID 1526646Notes

Reaction equation

HRID 1526646 reaction equation
[NH2:1][C:2]1[O:3][C@H:4]2[C@@H:6]([C@:7]([C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:31])[C:21]4[C:26]([CH2:27][O:28]C)=[CH:25][C:24]([Cl:30])=[CH:23][N:22]=4)[CH:15]=[CH:16][C:17]=3[F:18])([CH:9]([F:11])[F:10])[N:8]=1)[CH2:5]2.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[O:3][C@H:4]2[C@@H:6]([C@:7]([C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:31])[C:21]4[C:26]([CH2:27][OH:28])=[CH:25][C:24]([Cl:30])=[CH:23][N:22]=4)[CH:15]=[CH:16][C:17]=3[F:18])([CH:9]([F:11])[F:10])[N:8]=1)[CH2:5]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 90414451HCID 90414451, compound

Product 1

HCID 90413325HCID 90413325, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3-((1R,5S,6R)-3-amino-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-5-yl)-4-fluorophenyl)-5-chloro-3-(methoxymethyl) picolinamide (Example 42, 140 mg, 0.308 mmol) in DCM was cooled to 0° C. Boron tribromide (0.062 mL, 0.646 mmol) was added dropwise and the reaction mixture was allowed to warm to rt. After 3 hs, the reaction was quenched by the addition of water. The aq. phase was neutralized by the addition of aq. sat bicarbonate solution and extracted with EtOAc. The organic phase was over MgSO4. The filtrate material was absorbed onto a plug of silica gel and purified by chromatography eluting with a gradient of 15% to 100% EtOAc in hexane, to provide the title compound (62 mg, 0.141 mmol, 45.7% yield) as a whit solid. MS m/z=441 [M+H]+

Workup

  1. customAfter 3 hs, the reaction was quenched by the addition of water
  2. additionThe aq. phase was neutralized by the addition
  3. extractionextracted with EtOAc
  4. customThe filtrate material was absorbed onto a plug of silica gel
  5. custompurified by chromatography
  6. washeluting with a gradient of 15% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-fba35fe7b34248b49a978f0fcafc27a8
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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