Boron tribromide → HCID 66689542, compound

HRID 403544Notes

Reaction equation

HRID 403544 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH:16]([C:18]2[N:27]([C:28]3[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=3)[C:26](=[O:36])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH3:17])[CH3:15])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH:16]([C:18]2[N:27]([C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=3)[C:26](=[O:36])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH3:17])[CH3:15])(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10152394HCID 10152394, compound

Product 1

HCID 66689542HCID 66689542, compoundYield 139.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the 4-tert-butyl-N-{1-[3-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl]ethyl}-N-methylbenzenesulfonamide (0.5 g, 1.07 mmol) stirring in 15 mL DCM was added boron tribromide (5 mL, 5 mmol 1M in DCM). The reaction was allowed to stir at room temperature for 15 min after which TLC analysis indicated that starting material was completely consumed. The reaction was quenched with 20 mL brine and the resulting mixture was transferred to a separatory funnel. The layers were separated and the aqueous layer extracted with CHCl3 (2×25 mL). The combined organics were washed with brine, dried over MgSO4, and concentrated under vacuum to afford a crude residue that was purified by chromatography (silica gel, 0-75% EtOAc:Hex), yielding the desired product as a white solid (0.735 g, 95%). 1H-NMR (CDCl3): δ 8.26 (d, 1H), 7.67 (t, 1H), 7.51 (d, 2H), 7.45 (t, 1H), 7.36 (m, 2H), 7.26 (d, 2H), 6.98 (m, 1H), 6.90 (m, 2H), 5.00 (q, 1H), 3.19 (s, 3H), 1.28 (d, 3H), 1.17 (s, 9H); MS (ESI) 492 (MH+).

Workup

  1. customwas completely consumed
  2. customThe reaction was quenched with 20 mL brine
  3. customthe resulting mixture was transferred to a separatory funnel
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with CHCl3 (2×25 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under vacuum
  9. customto afford a crude residue that
  10. customwas purified by chromatography (silica gel, 0-75% EtOAc:Hex)

Sources & evidence

ORD record
ord-978b04138ad048318fa5a4902bfdeb33
Source dataset
uspto-grants-2014_06
Patent number
US08748440B2

Reaction notes

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