Water → HCID 22477600, compound

HRID 549063Notes

Reaction equation

HRID 549063 reaction equation
N1(C2C=CC([C:13]3[NH:21][C:16]4=NC=CN=[C:15]4[C:14]=3[CH2:22][CH2:23][C:24]([NH:26]C)=O)=CC=2)CCOCC1.[C:28]1([Mg]Br)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>O1CCCC1>[C:28]1([C:22]2[CH:23]=[CH:24][N:26]=[C:13]3[NH:21][CH:16]=[CH:15][C:14]=23)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22477350HCID 22477350, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 22477600HCID 22477600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 1-(2,6-dimethyl-1,4-dihydropyridin-4-one)-1H-pyrrolo[2,3-b]pyridinium tetrafluoroborate (Reference Example 43, 1.0 g) in tetrahydrofuran (100 mL) was treated with a solution of phenylmagnesium bromide in tetrahydrofuran (9.6 mL, 1M) and stirred at room temperature for 72 hours before adding water ((100 mL) and the tetrahydrofuran removed in vacuo. The residue was extracted with chloroform (3×100 mL), and the combined organics dried over sodium sulfate and evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (99:1 v/v) to give the title compound (83 mg) as a white solid. MS: 195 (MH+). 1H NMR [(CD3)2SO]: δ 8.27 (1H, d, J=4.1 Hz); 7.78 (2H, d, J=8.2 Hz); 7.57 (3H, m); 7.48 (1H, t, J=8.2 Hz); 7.19 (1H, d, J=3.5 Hz); 6.60 (1H, s).

Workup

  1. customthe tetrahydrofuran removed in vacuo
  2. extractionThe residue was extracted with chloroform (3×100 mL)
  3. dry with materialthe combined organics dried over sodium sulfate
  4. customevaporated
  5. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (99:1 v/v)

Sources & evidence

ORD record
ord-615ae9c30d884bca9d997c8714606122
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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