Sodium t-butoxide → HCID 24956160, compound

HRID 417933Notes

Reaction equation

HRID 417933 reaction equation
Br.O1C2C=CC(O)=CC=2[NH:5]CC1.C[C:14]([CH3:17])([O-:16])[CH3:15].[Na+].[CH3:19][C:20]1([CH3:46])[CH2:44][C:24]2[N:25]=[C:26]([N:28]3[C:33]4C=C(C5C=CC=CC=5)C=[CH:37][C:32]=4[O:31][CH2:30][CH2:29]3)[S:27][C:23]=2[C:22](=[O:45])[CH2:21]1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:46][C:20]1([CH3:19])[CH2:21][NH:5][C:22](=[O:45])[C:23]2[S:27][C:26]([N:28]3[C:33]4[CH:15]=[C:14]([OH:16])[CH:17]=[CH:37][C:32]=4[O:31][CH2:30][CH2:29]3)=[N:25][C:24]=2[CH2:44]1

Participants

6

Reactant 3

HCID 23676156Sodium t-butoxideHCID 24956158HCID 24956158, compoundHCID 666482293,4-Dihydro-2H-1,4-benzoxazin-6-ol--hydrogen bromide (1/1)

Product 1

HCID 24956160HCID 24956160, compoundYield 1.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
140 °C

Procedure

Following Method B, using 3,4-dihydro-2H-benzo[1,4]oxazin-6-ol hydrobromide (84 mg, 3.6 mmol), sodium tert-butoxide (125 mg, 1.3 mmol), Intermediate 5 (100 mg, 3.6 mmol), (But)3PBF4 (31 mg, 0.11 mmol) and palladium(II) acetate (12 mg, 0.055 mmol) in DME (2 mL) heated to 140° C. for 20 min under microwave irradiation. The crude material was purified by prep HPLC to give the title compound as a white solid (5 mg, 0.4%). δH (CDCl3) 1.11 (6H, s), 2.85 (2H, s), 3.12 (2H, s), 4.07-4.19 (2H, m), 4.20-4.30 (2H, m), 6.53-6.62 (1H, m), 6.80 (1H, d, J 8.85 Hz), 7.34-7.40 (1H, m). LCMS (ES+) 346 (M+H)+.

Workup

  1. customThe crude material was purified by prep HPLC

Sources & evidence

ORD record
ord-bf3b36021a974881a4224bc34dfa9af1
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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