2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-Indazole → HCID 58529766, compound

HRID 1973025Notes

Reaction equation

HRID 1973025 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:15][CH2:14]2)[N:5]2[C:10]=1[C:9]([NH2:11])=[N:8][CH:7]=[N:6]2.[CH2:25]([N:32]1[CH:40]=[C:39]2[C:34]([CH:35]=[C:36](B3OC(C)(C)C(C)(C)O3)[CH:37]=[CH:38]2)=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:25]([N:32]1[CH:40]=[C:39]2[C:34]([CH:35]=[C:36]([C:2]3[CH:3]=[C:4]([CH2:12][N:13]4[CH2:18][CH2:17][N:16]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH2:15][CH2:14]4)[N:5]4[C:10]=3[C:9]([NH2:11])=[N:8][CH:7]=[N:6]4)[CH:37]=[CH:38]2)=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 585293132-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-IndazoleHCID 58529926HCID 58529926, compound

Product 1

HCID 58529766HCID 58529766, compoundYield 11%

Procedure

In a manner similar to the procedure described for step 3 of Example 83 and using 5-bromo-7-{[4-(trifluoroacetyl)piperazin-1-yl]methyl}pyrrolo[2,1-f][1,2,4]triazin-4-amine and 2-benzyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-indazole as starting materials, 14 mg, (11%) of the desired product was isolated. 1H NMR (400 MHz, CD2Cl2) δ 8.05 (s, 1 H) 7.89 (s, 1 H) 7.74-7.81 (m, 2 H) 7.32-7.42 (m, 5 H) 7.24 (dd, 1 H) 6.71 (s, 1 H) 5.80 (br, 2 H) 5.62 (s, 2 H), 4.00 (s, 2 H) 3.59-3.71 (m, 4 H) 2.59-2.69 (m, 4 H). LC-MS [M+H]+=535.2, RT=2.51 min

Sources & evidence

ORD record
ord-8c5006bde5de4238b85f455006c18805
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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