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

HRID 645210Notes

Reaction equation

HRID 645210 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) 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-3ad1250c287044ec9296ab687f6e9095
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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