6-(Dimethylamino)pyridine-3-boronic acid → HCID 59263530, compound

HRID 545884Notes

Reaction equation

HRID 545884 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1([CH2:26][O:25][C:24]3[CH:27]=[C:28]4[C:32](=[CH:33][C:23]1=3)[CH2:31][CH2:30][O:29]4)[C:5](=[O:22])[N:6]2[CH2:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])=[O:13].BrC1C=CC=C2C=1C1(C3=CC4OCOC=4C=C3OC1)C(=O)N2CCCCC.[N:61]1[CH:66]=[C:65](B(O)O)[CH:64]=[N:63][CH:62]=1.CN(C)C1N=CC(B(O)O)=CC=1>>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[NH:14][C:12](=[O:13])[CH2:11][N:6]1[C:7]2[C:3](=[C:2]([C:65]3[CH:66]=[N:61][CH:62]=[N:63][CH:64]=3)[CH:10]=[CH:9][CH:8]=2)[C:4]2([CH2:26][O:25][C:24]3[CH:27]=[C:28]4[C:32](=[CH:33][C:23]2=3)[CH2:31][CH2:30][O:29]4)[C:5]1=[O:22]

Participants

5

Reactant 4

HCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 592633394'-bromo-1'-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)oneHCID 59263362HCID 59263362, compound

Product 1

HCID 59263530HCID 59263530, compound

Procedure

Following the procedure as described in EXAMPLE 4, and making non-critical variations using 2-(4′-bromo-2′-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-1′(2′H)-yl)-N-(2-fluorophenyl)acetamide to replace 4′-bromo-1′-pentylspiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and pyrimidine-5-boronic acid to replace [6-(dimethylamino)pyridin-3-yl]boronic acid, the title compound was obtained (53%) as a colorless solid: mp 229-230° C.; 1H NMR (300 MHz, CDCl3) δ 9.10 (s, 1H), 8.26-8.15 (m, 3H), 7.98 (s, 1H), 7.41 (t, 1H), 7.15-7.05 (m, 4H), 6.89 (d, 1H), 6.68 (s, 1H), 6.06 (s, 1H), 4.81-4.76 (m, 2H), 4.59-4.42 (m, 4H), 3.00 (t, 2H); 13C NMR (75 MHz, CDCl3) δ 178.2, 164.4, 162.5, 161.0, 157.0, 155.8, 141.8, 132.6, 131.1, 129.4, 125.8, 125.5, 125.4, 125.2, 125.1, 124.7, 121.9, 120.6, 119.9, 118.7, 115.1, 114.8, 109.5, 93.4, 79.0, 72.4, 57.8, 44.9, 28.9; MS (ES+) m/z 509.5 (M+1).

Sources & evidence

ORD record
ord-be3d33adb67e4a5e9dd7d4eb62f1719b
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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