3-Methoxyphenol → HCID 46194576, compound

HRID 1407926Notes

Reaction equation

HRID 1407926 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[CH3:14]OC1C=C(O)C=CC=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2([C:43]3[C:34](=[CH:35][C:36]4[O:41][CH2:40][CH2:39][O:38][C:37]=4[CH:42]=3)[O:33][CH2:32]2)[C:24]1=[O:44]>>[CH3:14][N:23]1[C:31]2[C:26](=[C:27]([O:13][C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)[CH:8]=3)[CH:28]=[CH:29][CH:30]=2)[C:25]2([C:43]3[C:34](=[CH:35][C:36]4[O:41][CH2:40][CH2:39][O:38][C:37]=4[CH:42]=3)[O:33][CH2:32]2)[C:24]1=[O:44]

Participants

4

Reactant 3

HCID 90073-MethoxyphenolHCID 1413433-MorpholinophenolHCID 58224164Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydro

Product 1

HCID 46194576HCID 46194576, compound

Procedure

Following the procedure as described in EXAMPLE 16.79 and making non-critical variations using 3-morpholinophenol to replace 3-methoxyphenol, morpholin-4-ylphenoxy)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (53%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ7.18-7.24 (m, 1H), 7.01-7.09 (m, 1H), 6.65 (d, J=7.7 Hz, 1H), 6.55 (d, J=8.5 Hz, 2H), 6.27 (s, 1H), 6.26-6.21 (m, 2H), 6.20 (s, 1H), 4.84 (ABq, 2H), 4.13-4.00 (m, 4H), 3.82-3.74 (m, 4H), 3.25 (s, 3H), 3.07-3.00 (m, 4H); 13C NMR (75 MHz, CDCl3) δ177.6, 157.5, 155.6, 153.3, 152.5, 144.8, 144.3, 137.6, 130.1, 129.7, 121.1, 119.4, 114.0, 111.0, 110.5, 109.7, 105.9, 103.6, 99.1, 77.6, 66.7, 64.4, 63.8, 57.3, 48.9, 27.0; MS (ES+) m/z 486.9 (M+1).

Workup

  1. customwas obtained (53%) as a colorless solid

Sources & evidence

ORD record
ord-0fb7466f64734a81909cb2b00055b63b
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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