5,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-one → HCID 59352643, compound

HRID 2385244Notes

Reaction equation

HRID 2385244 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]2[C:10]3([CH2:20][O:21][C:5]=2[CH:4]=1)[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:12][C:11]3=[O:19].N1C2C(=CC=CC=2)C2(COC3C=[C:36]4[C:40](=[CH:41][C:31]2=3)[CH2:39][CH2:38][O:37]4)C1=O>>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]2[C:10]3([CH2:20][O:21][C:5]=2[CH:4]=1)[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[N:12]([CH2:39][CH:38]1[CH2:31][CH2:41][CH2:40][CH2:36][O:37]1)[C:11]3=[O:19]

Participants

3

Reactant 2

HCID 592633545,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-oneHCID 593522256-Methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 59352643HCID 59352643, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, 6-methoxy-5-methyl-1′-(tetrahydro-2H-pyran-2-ylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (68%) as a colorless solid: mp 180-182° C.; 1H NMR (300 MHz, CDCl3) δ 7.28 (dd, J=7.8, 7.8 Hz, 1H), 7.13-6.97 (m, 3H), 6.47 (s, 1H), 6.43 (d, J=4.3 Hz, 1H), 4.91 (dd, J=8.9, 2.1 Hz, 1H), 4.66 (dd, J=8.9, 3.3 Hz, 1H), 4.02-3.59 (m, 4H), 3.79 (s, 3H), 3.43-3.31 (m, 1H), 1.99 (s, 3H), 1.92-1.77 (m, 1H), 1.71-1.26 (m, 5H); MS (ES+) m/z 380.4 (M+1).

Sources & evidence

ORD record
ord-5a299772b1a241a2afe195f5d398f8c7
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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