Nitrogen → HCID 117804464, compound

HRID 1527022Notes

Reaction equation

HRID 1527022 reaction equation
C([O-])([O-])=O.[K+].[K+].N#N.[CH3:9][C:10]1[N:11]([CH:32]([CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH3:33])[C:12]2[C:17]([C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[CH:16][CH:15]=[C:14](B1OC(C)(C)C(C)(C)O1)[CH:13]=2.Br[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O>[CH3:9][C:10]1[N:11]([CH:32]([CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH3:33])[C:12]2[C:17]([C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[CH:16][CH:15]=[C:14]([C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)[CH:13]=2

Participants

9

Reactant 4

HCID 947Nitrogen2×HCID 11430Potassium CarbonateHCID 122863-BromopyridineHCID 131733196HCID 131733196, compound

Product 1

HCID 117804464HCID 117804464, compoundYield 35.9%

Reagents, catalysts & solvents 4

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a re-sealable vial was added K2CO3 (206 mg, 1.488 mmol), PdCl2(dppf)-CH2Cl2 adduct (60.8 mg, 0.074 mmol), and the vial was sealed. This vial was evacuated/backfilled with N2 (3×) before addition of (R or S)-methyl 2-methyl-1-(1-(tetrahydro-2H-pyran-4-yl)ethyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carboxylate (318 mg, 0.744 mmol) dissolved in 1,4-dioxane (4 mL), 3-bromopyridine (71.7 μl, 0.744 mmol), and water (400 μL). The reaction was evacuated/backfilled with N2 (3×) before heating to 100° C. The solution was cooled to room temperature and diluted with EtOAc. The solution was filtered and concentrated in vacuo. The crude residue was purified via silica gel chromatography (10 g, EtOAc/hex (1:1)) to afford the title compound (101 mg, 0.267 mmol, 35.9% yield). LCMS 379 (M+1)+.

Workup

  1. customthe vial was sealed
  2. temperatureThe solution was cooled to room temperature
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified via silica gel chromatography (10 g, EtOAc/hex (1:1))

Sources & evidence

ORD record
ord-52e2efe9784b4639b22c1a1f1610dc7d
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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