Boron tribromide → HCID 23582409, compound

HRID 1754471Notes

Reaction equation

HRID 1754471 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[Cl:14])[N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)(=[O:17])=[O:16])[C:6]=1[CH3:26].B(Br)(Br)Br>C(Cl)Cl>[Cl:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[N:7]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)(=[O:17])=[O:16])[C:6]([CH3:26])=[C:5]([CH2:4][C:3]([OH:27])=[O:2])[C:13]=12

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67218945HCID 67218945, compound

Product 1

HCID 23582409HCID 23582409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of [4-chloro-1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-yl]-acetic acid methyl ester (40 mg, 0.09 mmol) in CH2Cl2 (1 mL), is added 1M BBr3 in CH2Cl2 (536 μL, 0.54 mmol). The solution is subjected to microwave irradiation in a sealed reaction vessel with stirring at 60° C. over 45 minutes. The reaction mixture is evaporated to dryness in vacuo. Water is added and the suspension sonicated then filtered, washed with water and dried in vacuo, furnishing [4-chloro-1-(3,4-dichloro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-yl]-acetic acid; MH+=433.

Workup

  1. customirradiation
  2. customin a sealed reaction vessel
  3. customThe reaction mixture is evaporated to dryness in vacuo
  4. additionWater is added
  5. customthe suspension sonicated
  6. filtrationthen filtered
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-578305fcb59547f699eb2969d4397ca9
Source dataset
uspto-grants-2015_10
Patent number
US09169251B2

Reaction notes

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