2-(Chloromethyl)furan → 1'-(2-furylmethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 645234Notes

Reaction equation

HRID 645234 reaction equation
N1C2C(=CC=CC=2)[C:3]2([O:20][C:12]3[CH:13]=CC4OCOC=4[C:11]=3[CH2:10]2)C1=O.Br[C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[C:25]1([C:36]3=[CH:37][C:38]4[O:42][CH2:41][O:40][C:39]=4[CH:43]=[C:35]3[O:34][CH2:33]1)[C:26](=[O:32])[NH:27]2.ClCC1OC=CC=1.BrCC1OC(C(F)(F)F)=CC=1>>[O:20]1[CH:3]=[CH:10][CH:11]=[C:12]1[CH2:13][N:27]1[C:28]2[C:24](=[CH:23][CH:31]=[CH:30][CH:29]=2)[C:25]2([C:36]3=[CH:37][C:38]4[O:42][CH2:41][O:40][C:39]=4[CH:43]=[C:35]3[O:34][CH2:33]2)[C:26]1=[O:32]

Participants

5

Reactant 4

HCID 2195202-(Chloromethyl)furanHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 592633724'-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1H)-oneHCID 86609009HCID 86609009, compound

Product 1

HCID 592633431'-(2-furylmethyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneYield 40%

Procedure

Following the procedure described in EXAMPLE 10.47, and making non-critical variations using spiro[furo[2,3-][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 4′-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and 2-chloromethylfuran to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound (40%) as a colorless solid: mp 110-112° C.; 1H NMR (300 MHz, CDCl3) δ 7.35-7.33 (m, 1H), 7.29-7.23 (m, 1H), 7.15 (d, 1H), 7.06-7.00 (m, 2H), 6.50 (s, 1H), 6.34-6.31 (m, 2H), 6.10 (s, 1H), 5.85 (dd, 2H), 4.92 (ABq, 2H), 4.79 (ABq, 2H); 13C NMR (75 MHz, CDCl3) δ 177.1, 155.9, 149.0, 148.9, 142.6, 142.3, 141.8, 132.2, 128.9, 123.8, 123.5, 119.5, 110.6, 109.3, 108.7, 103.1, 101.5, 93.6, 80.4, 58.2, 37.1; MS (ES+) m/z 362.5 (M+1).

Sources & evidence

ORD record
ord-446c852dfcbe4ef68e1c268c91f1f642
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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