(2-Bromoethoxy)-tert-butyldimethylsilane → HCID 58529338, compound

HRID 1972844Notes

Reaction equation

HRID 1972844 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:33][CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37]>>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][N:29]([CH2:33][CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 58529326HCID 58529326, compound

Product 1

HCID 58529338HCID 58529338, compoundYield 52%

Procedure

5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (50 mg, 0.122 mmol) was reacted with (2-bromoethoxy)(tert-butyl)dimethylsilane (60 mg, 0.254 mmol), following the procedure of Example 136. The product was triturated with ether-hexanes to yield 36 mg (52%) of pure product. 1H NMR (300 MHz, DMSO-d6) δ 8.52 (s, 1 H), 7.87 (s, 1 H), 7.79 (d 1 H), 7.56 (m, 2 H), 7.33 (m, 4 H) 7.15 (d, 1 H), 6.67 (s, 1 H), 5.63 (s, 2 H) 4.10-3.2 (m, 7 H), 3.00-1.75 (m, 4 H), 0.85 (m, 9 H), 0.05 (s, 6 H); ES-MS m/z 568.3 [M+H]+, HPLC RT (min) 3.11.

Workup

  1. customThe product was triturated with ether-hexanes

Sources & evidence

ORD record
ord-ac06493d1c984205aba34d6890bf16e5
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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