7,8-dihydro-6H-spiro[furo[2,3-g]chromene-3,3'-indol]-2'(1'H)-one → HCID 59352610, compound

HRID 1407726Notes

Reaction equation

HRID 1407726 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:21]3[C:12](=[CH:13][C:14]4[CH2:15][CH2:16][CH2:17][O:18][C:19]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22].FC1C2OCCOC=2C=C2OCC3([C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[NH:38]C3=O)C=12>>[N:38]1[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=1[CH2:40][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:21]3[C:12](=[CH:13][C:14]4[CH2:15][CH2:16][CH2:17][O:18][C:19]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22]

Participants

3

Reactant 2

HCID 593524357,8-dihydro-6H-spiro[furo[2,3-g]chromene-3,3'-indol]-2'(1'H)-oneHCID 593527429-fluoro-2,3-dihydro-spiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1'H)-one

Product 1

HCID 59352610HCID 59352610, compound

Procedure

Following the procedure as described in EXAMPLE 5.25 and making non-critical variations using 7,8-dihydro-6H-spiro[furo[2,3-g]chromene-3,3′-indol]-2′(1′H)-one to replace 9-fluoro-2,3-dihydro-spiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, 1′-(pyridin-2-ylmethyl)-7,8-dihydro-6H-spiro-[furo[2,3-g]chromene-3,3′-indol]-2′(1′H)-one was obtained (87%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ8.46 (d, J=4.8 Hz, 1H), 7.71-7.77 (m, 1H), 7.37-6.88 (m, 6H), 6.64 (s, 1H), 6.18 (s, 1H), 5.03 (ABq, 2H), 4.72 (ABq, 2H), 4.04-3.84 (m, 2H), 2.66 (t, J=6.4 Hz, 2H), 1.88-1.67 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ177.1, 155.7, 154.3, 149.7, 149.4, 143.0, 137.5, 132.3, 129.1, 128.6, 123.9, 123.6, 123.4, 123.1, 122.0, 111.5, 110.4, 109.8, 79.3, 66.2, 58.0, 45.2, 25.2, 22.1; MS (ES+) m/z 384.8 (M+1).

Sources & evidence

ORD record
ord-42455eafbe8147d88f4f07a34644e5e6
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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