Methanol → Brt3qrq73F

HRID 2179446Notes

Reaction equation

HRID 2179446 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.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[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)-one

Product 1

HCID 69098169Brt3qrq73F

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, 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 (51.0 g, 140 mmol), sodium acetate (23.0 g, 281 mmol) and Pd(dppf)Cl2—CH2Cl2 (2.9 g, 3.5 mmol) in MeOH (560 mL) was pressurized to 120 psi of CO at 23° C. 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 23° C.
  2. filtrationthe precipitate collected by filtration
  3. washwashed with water
  4. customdried under nitrogen atmosphere

Sources & evidence

ORD record
ord-4f4f5a1768d04dd69dfebcbd1b56e992
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

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