Methanol → Methyl (2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylate

HRID 334846Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (2R)-5-iodo-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (100.0 g, 276 mmol), sodium acetate (45.3 g, 552 mmol) and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane adduct (11.3 g, 13.8 mmol) in a mixture of MeOH (1 L) and toluene (30 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=295.3 (M+1).

Workup

customwas pressurized to 120 psi of CO at 23° C.
filtrationthe precipitate collected by filtration
washwashed with water
customdried under nitrogen atmosphere

Sources & evidence

ORD record: ord-416348a5ab9c4572b5c1368e4202e418
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883807B2

Reaction notes

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