Methanol → Brt3qrq73F

HRID 588726Notes

Reaction equation

HRID 588726 reaction equation
I[C:2]1[CH:3]=[C:4]2[CH2:19][C@@:9]3([C:17]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:11][C:10]3=[O:18])[CH2:8][C:5]2=[N:6][CH:7]=1.[C:20]([O-:23])(=[O:22])C.[Na+].[CH3:25]O>O.ClCCl.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:18]=[C:10]1[NH:11][C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:17]2[C@@:9]21[CH2:8][C:5]1=[N:6][CH:7]=[C:2]([C:20]([O:23][CH3:25])=[O:22])[CH:3]=[C:4]1[CH2:19]2

Participants

6

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 58118681(6S)-3-Iodo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2' (1'H)-one2×

Product 1

HCID 69098169Brt3qrq73F

Reagents, catalysts & solvents 2

HCID 178478475HCID 178478475, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (6S)-3-iodo-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (described in Intermediate 4) (51.0 g, 140 mmol), sodium acetate (23.0 g, 281 mmol) and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane adduct (2.9 g, 3.5 mmol) in MeOH (560 mL) was pressurized to 120 psi of CO at ambient temperature and then heated at 80° C. for 12 h with stirring. The reaction mixture was diluted with water (1 L), and the precipitate collected by filtration, washed with water, and dried under nitrogen atmosphere to give the title compound, which was used without further purification. MS: m/z=296.1 (M+1).

Workup

  1. customwas pressurized to 120 psi of CO at ambient temperature
  2. filtrationthe precipitate collected by filtration
  3. washwashed with water
  4. customdried under nitrogen atmosphere

Sources & evidence

ORD record
ord-615721dcd58840459443a517bd1197d2
Source dataset
uspto-grants-2016_01
Patent number
US09227972B2

Reaction notes

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