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

HRID 588969Notes

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-4d2f6721795b47ce875f3e65ee93c299
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227973B2

Reaction notes

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