tert-Butyl acrylate → HCID 68412702, compound

HRID 340838Notes

Reaction equation

HRID 340838 reaction equation
Br.Br[C:3]1[CH:14]=[N:13][C:6]2[NH:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]=2[CH:4]=1.[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH:16]=[CH2:17]>>[C:20]([O:19][C:15](=[O:18])[CH:16]=[CH:17][C:3]1[CH:14]=[N:13][C:6]2[NH:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]=2[CH:4]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 15458tert-Butyl acrylateHCID 68413344HCID 68413344, compound

Product 1

HCID 68412702HCID 68412702, compoundYield 55%

Procedure

7-bromo-4-methyl-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepine hydrobromide (2.0 g, 6.2 mmol) was subjected to Heck coupling with tert-butyl acrylate to give crude product. Purification by silica gel chromatography (CH2Cl2:MeOH:NH4OH/95:4.95:0.05) gave the title compound as a brown oil (970 mg, 55%), 1H NMR (300 MHz, CDCl3) 8.11 (d, J=2.1 Hz, 1H), 7.52 (d, J=2.2 Mz, 1H), 7.47 (d, J=16.0 Hz, 1H) 6.22 (d, J=16.0 Hz, 1H), 3.64 (s, 2H), 3.27-3.31 (m, 2H), 2.83-2.88 (m, 2H), 2.44 (s, 3H), 1.52 (s, 9H); MS (ESI) m/e 290 (C16H23N3O2+H)+.

Workup

  1. customto give crude product
  2. customPurification by silica gel chromatography (CH2Cl2:MeOH:NH4OH/95:4.95:0.05)

Sources & evidence

ORD record
ord-70c78ad9ad8245d4b0d99abe4bc2d15e
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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