Dimethylacetamide → HCID 24946160, compound

HRID 1667459Notes

Reaction equation

HRID 1667459 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].Cl.[F:15][C:16]1[CH:17]=[C:18](NC)[C:19]2[O:24][CH2:23][O:22][CH2:21][C:20]=2[CH:25]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].C[C:81]([N:83](C)C)=O>CCOC(C)=O>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:83][CH2:81][C:18]3[C:19]4[O:24][CH2:23][O:22][CH2:21][C:20]=4[CH:25]=[C:16]([F:15])[CH:17]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

Participants

7

Reactant 5

HCID 31374DimethylacetamideHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-oneHCID 67416939HCID 67416939, compound

Product 1

HCID 24946160HCID 24946160, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), (6-fluoro-4H-benzo[1,3]dioxin-8-yl)-methylamine hydrochloride (141 mg, 0.64 mmol), Pd-2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-[(6-fluoro-4H-benzo[1,3]dioxin-8-ylmethyl)-amino]-2H-phthalazin-1-one: 14 mg (6.7%): m/z (M+H)=362. 1H-NMR (DMSO-d6) δ: 12.35 (s, 1H), 7.93 (d, 1H), 7.55 (m, 1H), 7.14 (dd, 1H), 6.97 (dd, 1H), 6.88 (dd, 1H), 6.84 (s, 1H), 5.34 (s, 2H), 4.89 (s, 2H), 4.35 (dd, 2H).

Workup

  1. temperatureto cool
  2. washwashed with water (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6543845731524b86983ea0fb1b4a581e
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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