2-Chloro-5-(tributylstannyl)-1,3-thiazole → 5-(5-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-chlorothiazole

HRID 1529329Notes

Reaction equation

HRID 1529329 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2I.[Cl:18][C:19]1[S:20][C:21]([Sn](CCCC)(CCCC)CCCC)=[CH:22][N:23]=1>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[N:6]=[C:5]2[C:21]1[S:20][C:19]([Cl:18])=[N:23][CH:22]=1

Participants

5

Reactant 2

HCID 116544212-Chloro-5-(tributylstannyl)-1,3-thiazoleHCID 679597555-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Product 1

HCID 679596995-(5-Bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-chlorothiazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared analogously to compound 30a, using 5-bromo-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (2.56 g, 6.29 mmol), 2-chloro-5-(tributylstannyl)thiazole (2.955 g, 7.23 mmol, Synthonix), CuI (0.12 g, 0.630 mmol) and Pd(PPh3)4 (0.74 g, 0.640 mmol). Purification by flash chromatography (Isco, (120 gram)) eluting with 2M NH3 in MeOH:DCM (0:1→1:99) gave 2.12 g (85%) of a white amorphous solid. m/z: 397.8, 399.8 [M+1].

Workup

  1. customPurification by flash chromatography (Isco, (120 gram))
  2. washeluting with 2M NH3 in MeOH:DCM (0:1→1:99)

Sources & evidence

ORD record
ord-f2f911d088144b4f8512ddae7db8ce5a
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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