2-Fluorophenylboronic acid → HCID 59352678, compound

HRID 1965681Notes

Reaction equation

HRID 1965681 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.N1C=CC(B(O)O)=CC=1.Br[C:21]1[CH:48]=[CH:47][C:24]([CH2:25][N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]3([CH2:38][O:37][C:36]4[CH:39]=[C:40]5[C:44](=[CH:45][C:35]3=4)[CH2:43][CH2:42][O:41]5)[C:27]2=[O:46])=[CH:23][CH:22]=1.BrC1OC(CN2C3C(=CC=CC=3)C3(COC4C=C5C(=CC3=4)CCO5)C2=O)=CC=1>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:21]1[CH:48]=[CH:47][C:24]([CH2:25][N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]3([CH2:38][O:37][C:36]4[CH:39]=[C:40]5[C:44](=[CH:45][C:35]3=4)[CH2:43][CH2:42][O:41]5)[C:27]2=[O:46])=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 27343542-Fluorophenylboronic acidHCID 2734379(Pyridin-4-yl)boronic acidHCID 59352659HCID 59352659, compoundHCID 68596795HCID 68596795, compound

Product 1

HCID 59352678HCID 59352678, compound

Procedure

Following the procedure as described in EXAMPLE 11.15 and making non-critical variations using 2-fluorophenylboronic acid to replace pyridin-4-ylboronic acid, and 1′-(4-bromobenzyl)-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one to replace 1′-[(5-bromofuran-2-yl)methyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, 1′-[(2′-fluorobiphenyl-4-yl)methyl]-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one was obtained (34%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.72-7.91 (m, 12H), 7.61 (s, 1H), 7.54 (s, 1H), 6.11 (ABq, 2H), 5.97 (ABq, 2H), 5.64 (t, J=8.6 Hz, 2H), 4.20-4.01 (m, 2H); 13C NMR (75 MHz, CDCl3) δ177.9, 161.8, 161.3, 158.0, 142.1, 135.3 (2C), 135.2, 132.8, 130.6 (2C), 129.5, 129.4, 129.2, 129.1, 128.7, 128.4, 128.3, 127.5, 124.4 (2C), 123.9, 123.4, 120.2, 119.9, 118.9, 116.3, 116.0, 109.3, 93.2, 80.6, 72.4, 57.7, 43.9, 29.0.

Sources & evidence

ORD record
ord-c22239825e8941f1a4ea5ecebe4068a3
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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