Water → HCID 22260270, compound

HRID 1609874Notes

Reaction equation

HRID 1609874 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:21]#[N:22])[N:5]([CH3:20])[C:6]=1[C:7]1[CH:8]=[CH:9][C:10]2[NH:15][C:14](=[O:16])[O:13][C:12]([CH3:18])([CH3:17])[C:11]=2[CH:19]=1.[CH3:23][Sn](C)(C)C.O>CN(P(N(C)C)(N(C)C)=O)C>[CH3:17][C:12]1([CH3:18])[C:11]2[CH:19]=[C:7]([C:6]3[N:5]([CH3:20])[C:4]([C:21]#[N:22])=[CH:3][C:2]=3[CH3:23])[CH:8]=[CH:9][C:10]=2[NH:15][C:14](=[O:16])[O:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 11661TetramethyltinHCID 12044968HCID 12044968, compound

Product 1

HCID 22260270HCID 22260270, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 4-bromo-5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile (70 mg, 0.2 mmol), PhCNPdCl(PPh3)2 (cat., 7 mg) and tetramethyltin (10 eq, 0.35 g, 2 mmol) in HMPA (3 mL) was heated to 110° C. for 5 days. The solution was allowed to cool, poured into water (20 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layer was washed with brine, dried over MgSO4 and purified by flash column chromatography on silica gel eluting with 30% ethyl acetate/hexane to give 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1,4-dimethyl-1H-pyrrole-2-carbonitrile (36 mg, 63%) as a white solid. 1H NMR (300 MHz, d6-DMSO) δ1.64 (s, 6H), 1.97 (s, 3H), 3.56 (s, 3H), 6.87 (s, 1H), 7.00 (d, 2H, J=8.1 Hz), 7.28 (dd, 1H, J=8.1, 1.6 Hz), 7.32 (s, 1H), 10.40 (s, 1H:) MS (ESI (−)) 294 (M−H)−. Anal. calcd for C17H17N3O2, C, 69.1, H, 5.8, N, 14.2. Found, C, 69.1, H, 5.72, N, 14.0.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate (3×5 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. custompurified by flash column chromatography on silica gel eluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-44f68252d08e4257a5bce98cafc5140b
Source dataset
uspto-grants-2006_01
Patent number
US06982261B2

Reaction notes

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