2-(Bromomethyl)tetrahydro-2H-pyran → HCID 59352651, compound

HRID 2385256Notes

Reaction equation

HRID 2385256 reaction equation
[C:1](=[O:13])([O:3][C:4]1([C:9](C)(C)C)[CH:6](CBr)[CH2:5]1)[NH2:2].Br[CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18]O1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2([C:34]3=[CH:35][C:36]4[O:40][CH2:39][O:38][C:37]=4[CH:41]=[C:33]3[O:32][CH2:31]2)[C:23]1=[O:42].N1C2C(=CC=CC=2)C2(COC3C=C4C(=CC2=3)CCO4)C1=O>>[CH:20]1([CH:21]([NH:2][C:1](=[O:13])[O:3][C:4]([CH3:9])([CH3:6])[CH3:5])[CH2:16][CH2:15][N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]3([C:34]4=[CH:35][C:36]5[O:40][CH2:39][O:38][C:37]=5[CH:41]=[C:33]4[O:32][CH2:31]3)[C:23]2=[O:42])[CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 592633545,6-dihydro-2H-spiro[benzofuro[6,5-b]furan-3,3'-indolin]-2'-oneHCID 67357939HCID 67357939, compound

Product 1

HCID 59352651HCID 59352651, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using tert-butyl-3-bromomethyl-1-cyclopropyl carbamate to replace 2-(bromomethyl)tetrahydro-2H-pyran, and spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2′(1′H)-one, tert-butyl [1-cyclopropyl-3-(2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)propyl]carbamate was obtained (91%) as a fluffy yellow solid: 1H NMR (300 MHz, CDCl3) δ7.28 (dd, J=7.7, 7.7 Hz, 1H), 7.13 (d, J=6.9 Hz, 1H), 7.02 (dd, J=7.2, 7.2 Hz, 1H), 6.90 (d, J=7.8 Hz, 1H), 6.47 (s, 1H), 6.11 (d, J=4.9 Hz, 1H), 5.83 (d, J=5.5 Hz, 2H), 4.88 (dd, J=8.9, 7.0, Hz, 1H), 4.69 (br, 1H), 4.62 (dd, J=8.9, 1.7 Hz, 1H), 3.93-3.73 (m, 2H), 2.99 (br, 1H), 2.14-1.81 (m, 2H), 1.30 (s, 9H), 0.95-0.80 (m, 1H), 0.58-0.19 (m, 4H); 13C NMR (75 MHz, CDCl3) δ177.3, 177.3, 155.9, 155.7, 155.6, 148.8, 142.3, 142.2, 132.4, 129.0, 123.9, 123.3, 119.5, 119.4, 108.6, 103.1, 103.0, 101.5, 93.6, 80.4 (2C), 65.9, 58.2, 37.8, 37.5, 32.9, 32.7, 28.4, 16.1 (2C), 15.3, 3.9, 3.8, 3.0, 2.9; MS (ES+) m/z 501.3, (M+23), 479.28 (M+1), 423.2 (M−56), 379.3 (M−100).

Sources & evidence

ORD record
ord-ff8a0c613c754614bd73eb49ae826882
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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