Boron tribromide → HCID 118159674, compound

HRID 628273Notes

Reaction equation

HRID 628273 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][C:19]4[N:20]([C:21]([CH3:24])=[N:22][N:23]=4)[C:15]=3[CH:14]=[C:13]2[CH3:25])=[CH:9][CH:8]=1>C(Cl)Cl>[CH3:24][C:21]1[N:20]2[C:15]3[CH:14]=[C:13]([CH3:25])[N:12]([CH2:11][C:10]4[CH:26]=[CH:27][C:7]([OH:6])=[CH:8][CH:9]=4)[C:16]=3[CH:17]=[CH:18][C:19]2=[N:23][N:22]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118159454HCID 118159454, compound

Product 1

HCID 118159674HCID 118159674, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.0 M Boron tribromide in DCM (0.54 mL, 0.54 mmol, Aldrich) was added to a solution of 6-(4-methoxybenzyl)-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (42 mg, 0.137 mmol, from Example 34) in DCM (4 mL) at −78° C., and the reaction was allowed to slowly reach room temperature. The reaction was quenched by the addition of water, followed by saturated NaHCO3 solution. DCM was removed in vacuo and the mixture was diluted with MeOH, filtered and purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (27 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 7.21 (d, J=9.7 Hz, 1H), 7.14 (d, J=9.7 Hz, 1H), 6.81 (d, J=8.6 Hz, 2H), 6.72 (d, J=8.6 Hz, 2H), 6.56 (s, 1H), 5.23 (s, 2H), 2.95 (s, 3H), 2.45 (s, 3H); LCMS (M+H)+: 293.1.

Workup

  1. customwas allowed to slowly reach room temperature
  2. customThe reaction was quenched by the addition of water
  3. customDCM was removed in vacuo
  4. additionthe mixture was diluted with MeOH
  5. filtrationfiltered
  6. custompurified by preparative HPLC-MS (Waters XBridge C18
  7. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (27 mg, 67%)

Sources & evidence

ORD record
ord-3dc576b465e94f2eb7f105728c0ce3e2
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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