Tetrabutylammonium Fluoride → 10-Bromo-6-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575281Notes

Reaction equation

HRID 575281 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:9][N:8]3[CH:21]=[CH:22][N:23]=[C:7]3[C:6]=2[CH:24]=1.ClC1C=CC2OCCC3N(C=C(C([O:42][CH3:43])=O)N=3)C=2N=1.CCCC[N+:48](CCCC)(CCCC)CCCC.[F-]>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:18])[CH3:19])([CH3:15])[CH3:16])[CH2:9][N:8]3[CH:21]=[C:22]([C:43]([NH2:48])=[O:42])[N:23]=[C:7]3[C:6]=2[CH:24]=1

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 86693202Methyl 2-chloro-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-9 carboxylateHCID 8669331010-Bromo-6-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine

Product 1

HCID 8669330910-Bromo-6-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

10-bromo-6-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was prepared from 10-bromo-6-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine using the same procedures as outlined for the synthesis of methyl 2-chloro-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-9 carboxylate. TBAF (1.7 g, 6.50 mmol, 2.00 equiv) was added in several batches to a stirred solution of this intermediate (1.6 g, 3.54 mmol, 1.00 equiv) in tetrahydrofuran (7 mL) at room temperature. After 1 h the resulting solution was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate and concentrated under vacuum.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2b7948c53a7a4632b8d0546b3e65233b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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