Dibenzofuran-4-boronic acid → HCID 59263453, compound

HRID 545874Notes

Reaction equation

HRID 545874 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([C:15]3=[CH:16][C:17]4[O:21][CH2:20][O:19][C:18]=4[CH:22]=[C:14]3[O:13][CH2:12]1)[C:5](=[O:11])[NH:6]2.BrC1C=[CH:31][CH:30]=[C:29]2[C:25]=1[C:26]1([C:42]3=[CH:43][C:44]4OCO[C:45]=4[CH:49]=[C:41]3[O:40][CH2:39]1)C(=O)N2CCCCC.C1C2C3C=CC=CC=3OC=2C(B(O)O)=CC=1.CN(C)C1N=CC(B(O)O)=CC=1>>[CH:43]1[C:42]2[C:26]3[CH:25]=[CH:29][CH:30]=[CH:31][C:39]=3[O:40][C:41]=2[C:49]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[C:4]2([C:15]4=[CH:16][C:17]5[O:21][CH2:20][O:19][C:18]=5[CH:22]=[C:14]4[O:13][CH2:12]2)[C:5](=[O:11])[NH:6]3)=[CH:45][CH:44]=1

Participants

5

Reactant 4

HCID 2734328Dibenzofuran-4-boronic acidHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 592633394'-bromo-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)oneHCID 592633724'-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1H)-one

Product 1

HCID 59263453HCID 59263453, compound

Procedure

Following the procedure as described in EXAMPLE 4, and making non-critical variations using 4′-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 4′-bromo-1′-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and dibenzo[b,d]furan-4-ylboronic acid to replace [6-(dimethylamino)pyridin-3-yl]boronic acid, the title compound was obtained (10%) as a colorless solid: mp >230° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.77 (s, 1H), 8.04 (d, 1H), 7.97 (dd, 1H), 7.43-7.42 (m, 3H), 7.34-7.29 (m, 3H), 7.16 (t, 1H), 6.98 (d, 1H), 6.89 (d, 1H), 6.25 (s, 1H), 5.69 (d, 2H), 4.41 (ABq, 2H); MS (ES+) m/z 448.5 (M+1).

Sources & evidence

ORD record
ord-c87d2add515f4a0c8dbd5ef6a03acd54
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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