tert-Butanol → 1-(6-Morpholino-2',3',5',6'-tetrahydrospiro-[indoline-3,4'-pyran]-1-yl)ethanone

HRID 1618500Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]2[N:8]([C:16](=[O:18])[CH3:17])[CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C1(P(C2CCCCC2)C2C=CC(C3C(C(C)C)=CC(C(C)C)=CC=3C(C)C)=CC=2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:22]1[CH2:23][CH2:24][N:19]([C:2]2[CH:7]=[C:6]3[N:8]([C:16](=[O:18])[CH3:17])[CH2:9][C:10]4([CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)[C:5]3=[CH:4][CH:3]=2)[CH2:20][CH2:21]1

Participants

Conditions

Temperature: 110 °C

Procedure

1-(6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-yl)ethanone (2.56 g, 8.25 mmol) was combined with morpholine (1.08 mL, 12.4 mmol), dicyclohexyl-(2′,4′,6′-triisopropylbiphenyl-4-yl)phosphine (0.118 g, 0.248 mmol), Pd2dba3 (0.256 g, 0.248 mmol), and cesium carbonate (4.03 g, 12.4 mmol) in tert-butanol (30.0 mL, 314 mmol). The reaction was purged with N2, and heated at 110° C. for 4 h. After this time the reaction was diluted with EtOAc and filtered through a Celite pad. The filtrate was concentrated in vacuo. The crude material was triturated with EtOAc/hexane to give 1-(6-morpholino-2′,3′,5′,6′-tetrahydrospiro-[indoline-3,4′-pyran]-1-yl)ethanone. Mass Spectrum (ESI) m/e=317 (M+1).

Workup

customThe reaction was purged with N2
additionAfter this time the reaction was diluted with EtOAc
filtrationfiltered through a Celite pad
concentrationThe filtrate was concentrated in vacuo
customThe crude material was triturated with EtOAc/hexane

Sources & evidence

ORD record: ord-0b0f6204bba94ade879453578a6fa919
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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