1-Bromopentane → HCID 59352421, compound

HRID 2385334Notes

Reaction equation

HRID 2385334 reaction equation
N1C2C(=CC=CC=2)C2(C3C(=CC4OCC(=O)OC=4C=3)OC2)C1.[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].Br[CH2:46][C:47]1[CH:52]=[C:51]([F:53])[CH:50]=[C:49]([F:54])[CH:48]=1.BrCCCCC>>[F:53][C:51]1[CH:52]=[C:47]([CH:48]=[C:49]([F:54])[CH:50]=1)[CH2:46][N: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]

Participants

5

Reactant 4

HCID 80571-BromopentaneHCID 5188963,5-Difluorobenzyl bromideHCID 59352191Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydro-, (3'S)-HCID 68598253HCID 68598253, compound

Product 1

HCID 59352421HCID 59352421, compound

Procedure

Following the procedure as described in EXAMPLE 7.3 and making non-critical variations using 2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2(1′H)-one to replace (S)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, and 1-(bromomethyl)-3,5-difluorobenzene to replace 1-bromopentane, 1′-(3,5-difluorobenzyl)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (72%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 7.22-7.32 (m, 1H), 7.24-7.14 (m, 2H), 7.13-7.00 (m, 4H), 6.53 (s, 1H), 6.11 (s, 1H), 4.96 (s, 2H), 4.77 (ABq, 2H), 4.23-4.07 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 176.6, 154.7, 144.2, 141.9, 137.8, 131.6, 128.9, 125.7, 125.6, 125.2, 124.4, 123.7, 123.2, 121.0, 116.9, 116.7, 111.1, 109.1, 98.8, 79.5, 64.2, 63.6, 57.2; MS (ES+) m/z 421.8 (M+1).

Sources & evidence

ORD record
ord-bbcdd638ec044416b25dbbd87f0643ed
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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