(3-Methoxyphenyl)boronic acid → HCID 135839328, compound

HRID 724413Notes

Reaction equation

HRID 724413 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:18]4[NH:22][C:21]5[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=5[N:19]=4)=[N:14][NH:15]3)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.COC1C=C(B(O)O)C=CC=1.COC1C=C(O)C=CC=1C1C=C2C(C(C3NC4C=CC=CC=4N=3)=NN2)=CC=1>>[NH:22]1[C:21]2[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=2[N:19]=[C:18]1[C:13]1[C:12]2[C:16](=[CH:17][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([OH:2])[CH:4]=3)=[CH:10][CH:11]=2)[NH:15][N:14]=1

Participants

4

Reactant 3

HCID 2734370(3-Methoxyphenyl)boronic acidHCID 135839295HCID 135839295, compoundHCID 136341903HCID 136341903, compound

Product 1

HCID 135839328HCID 135839328, compound

Procedure

Example 24(o) was prepared in a similar manner to that described for Example 24(f), except that 6-(3-methoxy-phenyl)-3-1H-benzoimidazol-2-yl-1H-indazole, prepared in a similar manner to that described for example 24(a) except that 3-methoxy-phenylboronic acid was used instead of 5-methoxy-2-methyl-4-[2-(trimethylsilanyl)-ethoxymethoxy]-phenylboronic acid in step (viii), was used instead of 6-(2-methoxy-4-hydroxyphenyl)-3-1H-benzoimidazol-2-yl-1H-indazole. 1H NMR (300 MHz, DMSO-d6) δ 13.67 (s, 1H), 13.00 (s, 1H), 9.58 (s, 1H), 8.55 (d, 1H, J=8.4 Hz), 7.71–7.75 (m, 2H), 7.49–7.57 (m, 2H), 7.30 (t, 1H, J=7.8 Hz), 7.12–7.24 (m, 4H), 6.80 (dd, 1H, J=8.1, 1.5 Hz). MS (ES) [m+H]/z calc'd 327. found 327. [m−H]/z calc'd 325. found 325.

Workup

  1. customExample 24(o) was prepared in a similar manner to that
  2. customprepared in a similar manner to that

Sources & evidence

ORD record
ord-33179c893f254b959d82c19a0969d38d
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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