Cesium carbonate → HCID 117683816, compound

HRID 1507537Notes

Reaction equation

HRID 1507537 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[N:7][C:6]=2[CH:10]=1.I[C:12]1[C:13]([NH:26][C@@H:27]2[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]2)=[N:14][C:15]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[N:16][C:17]=1[O:18][CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.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.[Cu]I>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:12]3[C:13]([NH:26][C@@H:27]4[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]4)=[N:14][C:15]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[N:16][C:17]=3[O:18][CH3:19])=[N:7][C:6]=2[CH:10]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 36101555-BromobenzothiazoleHCID 89554305HCID 89554305, compound

Product 1

HCID 117683816HCID 117683816, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Following the same procedure as in step 3 of Example 337 using 5-bromo-1,3-benzothiazole (74.9 mg, 0.35 mmol, 1.80 equiv), tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (100.0 mg, 0.19 mmol, 1.00 equiv), cesium carbonate (370 mg, 1.14 mmol, 6.00 equiv), Pd(PPh3)4 (40.4 mg, 0.035 mmol, 0.18 equiv), copper (I) iodide (6.7 mg, 0.035 mmol, 0.18 equiv) in DMF (5.0 mL). The crude product was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (10:1-5:1) to provide the title compound as a light yellow solid. MS m/z [M+H]+ (ESI): 605

Workup

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluting with petroleum ether/ethyl acetate (10:1-5:1)

Sources & evidence

ORD record
ord-a0fd4fa54616419b82963df0a1e32b31
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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