Tetrabutylammonium Fluoride → HCID 60141493, compound

HRID 1946933Notes

Reaction equation

HRID 1946933 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[CH2:13][O:12][CH2:11][C:10]([NH2:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]#[C:24][Si](C)(C)C)=[N:21][CH:22]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:2]2[CH:3]=[C:4]([C:8]3([CH3:15])[CH2:13][O:12][CH2:11][C:10]([NH2:14])=[N:9]3)[CH:5]=[CH:6][CH:7]=2)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 10943735HCID 10943735, compoundHCID 68153814HCID 68153814, compound

Product 1

HCID 60141493HCID 60141493, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner analogous to that described in Example 42, the reaction of (RS)-5-(3-iodo-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine (intermediate XII-2) with 5-chloro-2-trimethylsilanylethynyl-pyridine (EP385210) was performed. In addition, after combination of solution 1 and 2, a solution of tetrabutylammonium fluoride in tetrahydrofuran (1M, 0.47 ml) was added. The 5-[3-(5-chloro-pyridin-2-ylethynyl)-phenyl]-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine was obtained as a white foam. MS (ISP): m/z=326.3 [M+H]+.

Sources & evidence

ORD record
ord-f466c8f8b97c4d8f8cbd9d57e5f4d751
Source dataset
uspto-grants-2013_03
Patent number
US08399459B2

Reaction notes

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