HCID 68851362, compound → HCID 86616907, compound

HRID 1984689Notes

Reaction equation

HRID 1984689 reaction equation
C(N1C(C)=C(I)N=C1CCC)C.[CH3:13][C:14]1[N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:17]2=[N:16][C:15]=1[C:23]#[C:24][Si](C)(C)C>>[C:23]([C:15]1[N:16]=[C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][N:18]2[C:14]=1[CH3:13])#[CH:24]

Participants

3

Reactant 2

HCID 68851362HCID 68851362, compound2×HCID 68852660HCID 68852660, compound

Product 1

HCID 86616907HCID 86616907, compoundYield 51%

Procedure

As described for example 3a, 1-ethyl-4-iodo-5-methyl-2-propyl-1H-imidazole (2.60 g, 9.92 mmol) instead of 2-amino-5-bromopyridine was converted to 3-methyl-2-trimethylsilanyl-ethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine (SiO2, dichloromethane:methanol=100:0 to 98:2, 890 mg, 39%) which was obtained as a dark brown semisolid and used further without detailed characterization. As described for example 3b, 3-methyl-2-trimethylsilanylethynyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine (890 g, 3.83 mmol) instead of 5-trimethylsilanyl-ethynyl-pyridin-2-ylamine was converted to the title compound (SiO2, ethyl acetate, 310 mg, 51%) which was obtained as a light brown solid. MS: m/e=161.3 [M+H]+.

Workup

  1. customwas obtained as a dark brown semisolid

Sources & evidence

ORD record
ord-a00bd8853c1f42a2b8683dbc8b8bbd97
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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